Скачиваний:
24
Добавлен:
15.08.2013
Размер:
533.84 Кб
Скачать

14. Some synthetic uses of double-bonded functional groups

765

VII. REFERENCES

1.N. Anand, J. S. Bindra and S. Ranganathan, Art in Organic Synthesis, Wiley, Chichester, 1988.

2.R. C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, VCH, New York, 1989.

3. B. M. Trost and I. Fleming (Eds.), Comprehensive Organic Synthesis, Vol. 5 (Vol. Ed.

L. A. Paquette), Pergamon Press, Oxford, 1991.

4.K. N. Houk, Y. Li and J. D. Evanseck, Angew. Chem., Int. Ed. Engl., 31, 682 (1992).

5.F. Fringuelli, L. Minuti, F. Pizzo and A. Taticchi, Acta Chem. Scand., 47, 255 (1993).

6.U. Pindur, G. Lutz and C. Otto, Chem. Rev., 93, 741 (1993).

7.W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990.

8.S. Otto, W. Blokzijl and J. B. F. N. Engberts, J. Org. Chem., 59, 5372 (1994).

9.T. Schwenkreis and A. Berkessel, Tetrahedron Lett., 34, 4785 (1993).

10.A. S. Kende, P. Delair and B. E. Blass, Tetrahedron Lett., 35, 8123 (1994).

11.A. Galinda, L. Astudillo, A. Galindo, A. G. Gonzalez and H. Mansilla, Heterocycles, 36, 1075 (1993).

12.R. Irie, N. Hosoya and T. Katsuki, Synlett, 255 (1994).

13.Y. Kurusu, Y. Masuyama, K. Yanagi, H. Morinaga, S. Yamamoto and M. Makanishi, Bull. Chem. Soc. Jpn., 66, 673 (1993).

14.T. Sato, J. Dakka and R. A. Sheldon, J. Chem. Soc., Chem. Commun., 1887 (1994).

15.P. Wipf and Y. Kim, J. Org. Chem., 58, 1649 (1993).

16.D. A. Clark, F. De Riccardis and K. C. Nicolaou, Tetrahedron, 50, 11391 (1994).

17.P. Laszlo, M. Levart and G. P. Singh, Tetrahedron Lett., 32, 3167 (1991).

18.Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987).

19.B. Goument, L. Duhamel and R. Mauge, Tetrahedron, 50, 171 (1994).

20.T. Punniyamurthy, B. Bhatia and J. Iqbal, Tetrahedron Lett., 34, 4657 (1993).

21.T. Yamada, T. Takai, O. Rhode and T. Mukaiyama, Chem. Lett., 1 (1991).

22.T. Yamada, T. Takai, O. Rhode and T. Mukaiyama, Bull. Chem. Soc. Jpn., 64, 2109 (1991).

23.T. Mukaiyama, T. Takai, T. Yamada and O. Rhode, Chem. Lett., 1661 (1990).

24.R. W. Saalfrank, S. Reihs and M. Hug, Tetrahedron Lett., 34, 6033 (1993).

25.E. Bouhlel, P. Laszlo, M. Levart, M-T. Montaufier and G. P. Singh, Tetrahedron Lett., 34, 1123 (1993).

26.P. Laszlo and M. Levart, Tetrahedron Lett., 34, 1127 (1993).

27.P. L. Bailey, W. Clegg, R. F. W. Jackson and O. Meth-Cohn, J. Chem. Soc., Perkin Trans. 1, 343 (1993).

28.A. D. Briggs, R. F. W. Jackson, W. Clegg, M. R. J. Elsegood, J. Kelly and P. A. Brown, Tetrahedron Lett., 35, 6945 (1994).

29.T. Yamada, K. Imagawa, T. Nagata and T. Mukaiyama, Bull. Chem. Soc. Jpn., 67, 2248 (1994).

30.K. Imagawa, T. Nagata, T. Yamada and T. Mukaiyama, Chem. Lett., 527 (1994).

31.T. Yamada, K. Imagawa and T. Mukaiyama, Chem. Lett., 2109 (1992).

32.S. Inoki, T. Takai, T. Yamada and T. Mukaiyama, Chem. Lett., 941 (1991).

33.T. Takai, E. Hata, T. Yamada and T. Mukaiyama, Bull. Chem. Soc. Jpn., 64, 2513 (1991).

34.T. Yamada, T. Takai, O. Rhode and T. Mukaiyama, Bull. Chem. Soc. Jpn., 64, 2109 (1991).

35.K. Yorozu, T. Takai, T. Yamada and T. Mukaiyama, Bull. Chem. Soc. Jpn., 67, 2195 (1994).

36.K. Kaneda, S. Haruna, T. Imanaka, M. Hamamoto, Y. Nishiyama and Y. Ishii, Tetrahedron Lett., 33, 6827 (1992).

37.W. Adam and M. Richter, Acc. Chem. Res., 27, 57 (1994).

38.W. Adam, A. G. Griesbeck and X. Wang, Justus Liebigs Ann. Chem., 193 (1992).

39.W. Adam, M. Braun, A. Griesbeck, V. Lucchini, E. Staab and B. Will, J. Am. Chem. Soc., 111, 203 (1989).

40.W. Adam and M. J. Richter, J. Org. Chem., 59, 3341 (1994).

41.M. Schulz, R. Kluge and M. Lipke, Synthlett, 915 (1993).

42.S. Chang, N. H. Lee and E. N. Jacobsen, J. Org. Chem., 58, 6939 (1993).

43.B. D. Brandes and E. N. Jacobsen, J. Org. Chem., 59, 4378 (1994).

44.H. Sasaki, R. Irie, T. Hamada, K. Suzuki and T. Katsuji, Tetrahedron, 50, 11827 (1994).

45.D. S. Thomsen, B. Schiott and K. A. Jorgensen, J. Chem. Soc., Chem. Commun., 1072 (1992).

46.E. J. Allain, L. P. Hager, L. Deng and E. N. Jacobsen, J. Am. Chem. Soc., 115, 4415 (1993).

47.D. Ostovic and T. C. Bruce, J. Am. Chem. Soc., 110, 6907 (1988).

766

Jeff Hoyle

48.B. B. De, B. B. Lohray and P. K. Dhal, Tetrahedron Lett., 34, 2371 (1993).

49.D. R. Reddy and E. R. Thornton, J. Chem. Soc., Chem. Commun., 172 (1992).

50.T. Yamada, K. Imagawa, T. Nagata and T. Mukaiyama, Chem. Lett., 2231 (1992).

51.E. N. Jacobsen, W. Zhang and M. L. Guler, J. Am. Chem. Soc., 113, 6703 (1991).

52.W. Zhang, J. L. Loebach, S. R. Wilson and E. N. Jacobsen, J. Am. Chem. Soc., 112, 280 (1990).

53.R. Irie, K. Noda, Y. Ito, N. Matsumoto and T. Katsuki, Tetrahedron Asymmetry, 2, 481 (1991).

54.N. H. Lee and E. N. Jacobsen, Tetrahedron Lett., 32, 6533 (1991).

55.E. N. Jacobsen, in Catalytic Asymmetric Synthesis (Ed. I. Ojima), Chap. 4, VCH, New York, 1993.

56.K. S. Suslick and B. R. Cook, J. Chem. Soc., Chem. Commun., 200 (1987).

57.D. Mansuy, Pure Appl. Chem., 62, 741 (1990).

58.J. P. Collman, X. Zhang, R. T. Hambre and J. I. Brauman, J. Am. Chem. Soc., 112, 5356 (1990).

59.J. T. Groves and P. Viski, J. Org. Chem., 55, 3628 (1990).

60.W. Zhang, J. L. Loebach, S. R. Wilson and E. N. Jacobsen, J. Am. Chem. Soc., 112, 2801 (1990).

61.E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker and L. Deng, J. Am. Chem. Soc., 113, 7063 (1991).

62.W. Zhang and E. N. Jacobsen, J. Org. Chem., 56, 2296 (1991).

63.H. Sasaki, R. Irie and T. Katsuki, Synlett, 356 (1994).

64.D. Mohajer and S. Tangestaninejad, Tetrahedron Lett., 35, 945 (1994).

65.D. Mohajer and S. Tangestaninejad, J. Chem. Soc., Chem. Commun., 240 (1993).

66.B. C. B. Bezuidenhoudt, A. Swanepoel, J. A. N. Augustyn and D. Terreirra, Tetrahedron Lett., 28, 4857 (1987).

67.J. R. Flisak, K. Gombatz, I. Lantos, W. Mendelson and J. R. Remich, Tetrahedron Lett., 31, 6501 (1990).

68. J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson,

V. J. Novack, J. J. Remich and L. Snyder, J. Org. Chem., 58, 6247 (1993).

69.P. Bovicelli and P. Lupattelli, J. Org. Chem., 59, 4304 (1994).

70.P. Bovicelli, P. Lupattelli, E. Mincione, T. Prencipe and R. Curci, J. Org. Chem., 57, 2182 (1992).

71.M. Kurihara, S. Ito N. Tsutsumi and N. Miyata, Tetrahedron Lett., 35, 1577 (1994).

72.M. Abou El-Zahab, W. Adam and C. R. Saha-Moller, Justus Liebigs Ann. Chem., 445 (1991).

73.W. Adam, F. Prechtl, M. J. Richter and A. K. Smerz, Tetrahedron Lett., 34, 8427 (1993).

74.C. H. Marzabadi and C. D. Spilling, J. Org. Chem., 58, 3761 (1993).

75.R. G. Dushin and S. Danishefsky, J. Am. Chem. Soc., 114, 3471 (1992).

76.K. Chow and S. Danishefsky, J. Org. Chem., 55, 4211 (1990).

77.D. M. Gordon and S. Danishefsky, J. Carbohydr. Res., 206, 361 (1990).

78.M. Mandel, T. Hudlickly, L. D. Kwart and G. M. Whited, J. Org. Chem., 58, 2331 (1993).

79.C. Kandzin and E. Steckhan, Tetrahedron Lett., 35, 3695 (1994).

80.A. Koch, J.-L. Reymond and R. A. Lerner, J. Am. Chem. Soc., 116, 803 (1994).

81.S. Takano, Y. Iwabuchi and K. Ogasawara, J. Am. Chem. Soc., 113, 2686 (1991).

82.T. Yoshimitsu and K. Ogasawara, J. Chem. Soc., Chem. Commun., 2197 (1994).

83.T. H. Chan, L. M. Chen, D. Wang and L. H. Li, Can. J. Chem., 71, 60 (1993).

84.B. B. Lohray, V. Bhushan and E. Nandanan, Tetrahedron Lett., 35, 4209 (1994).

85.H. Becker, P. T. Ho, H. C. Kolb, S. Loren, P.-O. Norrby and K. B. Sharpless, Tetrahedron Lett., 35, 7315 (1994).

86.H. C. Kolb, P. G. Andersson and K. B. Sharpless, J. Am. Chem. Soc., 116, 1278 (1994).

87.H. C. Kolb, M. S. Van Nieuwenhze and K. B. Sharpless, Chem. Rev., 94, 2483 (1994).

88.P.-O. Norrby, H. C. Kolb and K. B. Sharpless, J. Am. Chem. Soc., 116, 8470 (1994).

89.K. Morikawa and K. B. Sharpless, Tetrahedron Lett., 34, 5575 (1993).

90.B. B. Lohray, E. Nandanan and V. Bhushan, Tetrahedron Lett., 35, 6559 (1994).

91.S. Y. Ko, M. Malik and A. F. Dickinson, J. Org. Chem., 59, 2570 (1994).

92.E. J. Corey and G. I. Lotto, Tetrahedron Lett., 31, 2665 (1992).

93.B. B. Lohray, A. Thomas, P. Chittari, J. R. Ahuja and P. K. Dhal, Tetrahedron Lett., 33, 5453 (1992).

94.E. J. Corey, M. C. Noe and S. Sarahar, J. Am. Chem. Soc., 115, 3828 (1993).

95. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 57, 2768 (1992).

14. Some synthetic uses of double-bonded functional groups

767

96.M. P. Arrington, Y. L. Bennani, T. Gogel, P. Walsh, S.-H. Zhao and K. B. Sharpless, Tetrahedron Lett., 34, 7375 (1993).

97.G. A. Crispino, K.-S. Jeong, H. C. Kolb, Z.-M. Wang, D. Xu and K. B. Sharpless, J. Org. Chem., 58, 3785 (1993).

98.S. C. Sinha and E. Keinan, J. Am. Chem. Soc., 115, 4891 (1993).

99.D. Pini, A. Petri and P. Salvadori, Tetrahedron, 50, 11321 (1994).

100.N. Ikemoto and S. L. Schreiber, J. Am. Chem. Soc., 112, 9657 (1990).

101.R. E. Ireland, P. Wipf and T. D. Roper, J. Org. Chem., 55, 2284 (1990).

102.J. A. Soderquist, A. M. Rane and C. J. Lopez, Tetrahedron Lett., 34, 1893 (1993).

103.A. J. Cooper and R. G. Salomon, Tetrahedron Lett., 31, 3813 (1990).

104.A. E. DeCamp, S. G. Mills, A. T. Kawaguchi, R. Desmond, R. A. Reamer, L. DiMichele and

R.P. Volante, J. Org. Chem., 56, 3564 (1991).

105.M. E. Jung and J. M. Gardiner, Tetrahedron Lett., 35, 6755 (1994).

106.J. S. Brimacombe, G. McDonaldo and M. A. Rahman, Carbohydr. Res., 205, 422 (1990).

107.L. Q. Sun, W. S. Zhou and X. F. Pan, Tetrahedron: Asymmetry, 2, 973 (1991).

108.S. Y. Ko, A. W. M. Lee, S. Masamune, L. A. Reed, K. B. Sharpless and F. J. Walker, Tetrahedron, 46, 245 (1990).

109.M. Nakajima, K. Tomioka, Y. Iitaka and K. Koga, Tetrahedron, 49, 10793 (1993).

110.S. Hanessian, P. Meffre, M. Girard, S. Beaudoin, J.-Y. Sanceau and Y. Bennani, J. Org. Chem., 58, 1991 (1993).

111.T. Oishi, K. Iida and M. Hirama, Tetrahedron Lett., 34, 3573 (1993).

112.T. Oishi, M. Hirama, L. R. Sita and S. Masamune, Synthesis, 789 (1991).

113.M. Nakajima, K. Tomioka and K. Koga, Tetrahedron, 49, 10807, (1993).

114.P. J. Walsh, P. T. Ho, S. B. King and K. B. Sharpless, Tetrahedron Lett., 35, 5129 (1994).

115.J. P. Lellouche, A. Gigou-Barbedette and R. Gree, Bull. Soc. Chim. Fr., 129, 605 (1992).

116.K. P. M. Vanhessche, Z-M Wang and K. B. Sharpless, Tetrahedron Lett., 35, 3469 (1994).

117.P. Blundell, A. K. Ganguly and V. M. Girijavallabhan, Synlett, 263 (1994).

118.R. A. Johnson and K. B. Sharpless, in Comprehensive Organic Synthesis (Eds. B. M. Trost and

I.Fleming), Vol. 7, Pergamon Press, Oxford, 1990, p. 437.

119.W. Amberg, Y. L. Bennani, R. K. Chadha, G. A. Crispino, W. B. Davis, J. Hartung, K.-S. Jeong,

Y.Ogino, T. Shibata and K. B. Sharpless, J. Org. Chem., 58, 844 (1993).

120. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 57, 2768 (1992).

121.M. A. Brimble and M. R. Nairn, Aust. J. Chem., 46, 195 (1993).

122.G. J. Thomas, in Recent Progress in the Chemical Synthesis of Antibiotics (Eds. G. Lukacs and

M.Ohno), Springer-Verlag, Berlin, 1990, p. 468.

123.H. Rubinstein and J. S. Svendsen, Acta Chem. Scand., 48, 439 (1994).

124.M. Mandel and T. Hudlicky, J. Chem. Soc., Perkin Trans. 1, 741 (1993).

125.D. R. Boyd, N. D. Sharma, M. R. J. Dorrity, M. V. Hand, R. A. S. McMordie, J. F. Malone,

H.P. Porter, H. Dalton, J. Chima and G. N. Sheldrake, J. Chem. Soc., Perkin Trans. 1, 1065 (1993).

126.G. N. Sheldrake, in Chirality in Industry: The Commercial Manufacture and Application of Optically Active Compounds (Eds. A. N. Collins, G. N. Sheldrake and J. Crosby), Chap. 6, WileyInterscience, New York, 1992.

127.H. A. J. Carless, Tetrahedron: Asymmetry, 3, 795 (1992).

128.N. Chida, T. Tobe and S. Ogawa, Tetrahedron Lett., 35, 7249 (1994).

129.A. Baeyer and V. Villiger, Chem. Ber., 32, 3625 (1899).

130.C. H. Hassa, Org. React., 9, 73 (1957).

131.S. I. Murahashi, Y. Oda and T. Naota, Tetrahedron Lett., 33, 7557 (1992).

132.T. Yamada, T. Takai, O. Rhode and T. Mukaiyama, Chem. Lett., 5 (1991).

133.C. Bolm, G. Schlingloff and K. Weickhardt, Tetrahedron Lett., 34, 3405 (1993).

134.K. Kaneda, S. Ueno. T. Imanaka, E. Shimotsuma, Y. Nishiyama and Y. Ishii, J. Org. Chem., 59, 2915 (1994).

135.F. E. Ziegler and H. Kim, Tetrahedron Lett., 34, 7669 (1993).

136.K. N. Harrison and T. J. Marks, J. Am. Chem. Soc., 114, 9220 (1992).

137.D. A. Evans, A. R. Muci and R. Sturmer, J. Org. Chem., 58, 5307 (1993).

138.Y. Matsumoto, M. Naito and T. Hayashi, Organometallics, 11, 2732 (1992).

768

Jeff Hoyle

139.M. Satoh, Y. Nomoto, N. Miyaura and A. Suzuki, Tetrahedron Lett., 30, 3789 (1989).

140.D. A. Evans, G. C. Fu and A. H. Hoveyda, J. Am. Chem. Soc., 114, 6671 (1992).

141.D. A. Evans and G. C. Fu, J. Am. Chem. Soc., 113, 4042 (1991).

142.K. Burgess and M. Jaspars, Tetrahedron Lett., 34, 6813 (1993).

143.K. Burgess and M. J. Ohimeyer, Chem. Rev., 91, 1179 (1991).

144.I. D. Gridnev, N. Miyaura and A. Suzuki, Organometallics, 12, 589 (1993).

145.K. Burgessand and W. A. van der Donk, Tetrahedron Lett., 34, 6817 (1993).

146.D. A. Evans, G. C. Fu and B. A. Anderson, J. Am. Chem. Soc., 114, 6679 (1992).

147.K. Burgess, W. A. Donk, S. A. Westcott, T. B. Marder, R. T. Baker and J. C. Calabrese, J. Am. Chem. Soc., 114, 9350 (1992).

148.X.-L. Hou, D.-G. Hong, G.-B. Rong, Y.-L. Guo and L.-X. Dai, Tetrahedron Lett., 34, 8513 (1993).

149.S. A. Westcott, H. P. Blom, T. B. Marder and R. T. Baker, J. Am. Chem. Soc., 114, 8863 (1992).

150.J. Zhang, B. Lou, G. Guo and L. Dai, Acta Chim. Sin., 50, 913 (1992).

151.J. Zhang, B. Lou, G. Guo and L. Dai, J. Org. Chem., 56, 1670 (1991).

152.M. Plehiers and C. Hootele, Tetrahedron Lett., 34, 7569 (1993).

153.G. B. Fisher, C. T. Goralski, L. W. Nicholson and B. Singaram, Tetrahedron Lett., 34, 7693 (1993).

154.Y. Matsusita, K. Sugamoto and T. Matsui, Chem. Lett., 925 (1993).

155.Y. Matsushita, T. Matsui and K. Sugamoto, Chem. Lett., 1381 (1992).

156.Y. Matsushita, K. Sugamoto and T. Matsui, Chem. Lett., 2165 (1992).

157.U. T. Bhalerao and M. Sridhar, Tetrahedron Lett., 34, 4341 (1993).

158.D. G. Lee, T. Chen and Z. Wang, J. Org. Chem., 58, 2918 (1993).

159.L. Benati, P. C. Montevecchi, D. Nanni and P. Spagnolo, Tetrahedron Lett., 34, 3595 (1993).

160.T. T. Wenzel, J. Chem. Soc., Chem Commun., 862 (1993).

161.R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985, p. 59.

162.K. Zaw and P. M. Henry, J. Org. Chem., 55, 1842 (1990).

163.F. Schroder, R. Fettkother, K. Dettner, W. A. Konig and W. Francke, Justus Liebigs Ann. Chem., 1211 (1994).

164.T. Inokuchi, L. Ping, F. Hamaue, M. Izawa and S. Torii, Chem. Lett., 121 (1994).

165.K. Otsuka and A. Kobayashi, Chem. Lett., 1197 (1991).

166.H. Pellissier, P.-Y. Michellys and M. Santelli, Tetrahedron Lett., 35, 6481 (1994).

167.M. Ioele, G. Ortaggi, M. Scarsella and G. Sleiter, Gazz. Chim. Ital., 122, 531 (1992).

168.K. Tamao, T. Hayashi and Y. Ito, J. Chem. Soc., Chem. Commun., 795 (1988).

169.K. Kato and T. Mukaiyama, Chem. Lett., 2233 (1989).

170.J. Yoshida, S. Nakatani and S. Isoe, J. Org. Chem., 54, 5655 (1989).

171.S. Nakatani, J. Yoshida and S. Isoe, Tetrahedron, 49, 2011 (1993).

172.J. Yoshida, S. Nakatani and S. Isoe, J. Chem. Soc., Chem. Commun., 1468 (1988).

173.J. H. Jung, C.-J. Chang, D. L. Smith, J. L. McLaughlin, S. Pummangura, C. Chaichantipyuth and C. Patarapanich, J. Nat. Prod., 500 (1991).

174.J. H. Jung, S. Pummangura, C. Chaichantipyuth, C. Patarapanich, P. E. Fanwick, C.-J. Chang and J. L. McLaughlin, Tetrahedron, 46, 5043 (1990).

175.P. G. Baraldi, R. Bazzanini, A. Bigoni, S. Manfredini, D. Simoni and G. Spalluto, Synthesis, 1206 (1993).

176.S.-I. Murahashi, T. Naota and H. Hanaoka, Chem. Lett., 1767 (1993).

177.S.-I. Murahashi, T. Saito, H. Hanaoka, Y. Murakami, T. Naota, H. Kumobayashi and S. Akutagawa, J. Org. Chem., 58, 2929 (1993).

178.S. Baskaran, J. Das and S. Chandrasekaran, J. Org. Chem., 54, 5182 (1989).

179.T. Takai, T. Yamada and T. Mukaiyama, Chem. Lett., 1499 (1991).

180.S. Baskaran, J. Das and S. Chandrasekaran, J. Org. Chem., 54, 5184 (1989).

181.B. B. Lohray, V. Bhushan and R. K. Kumar, J. Org. Chem., 59, 1375 (1994).

182.B. R. Babu and K. K. Balasubramanian, Org. Prep. Proc. Int., 26, 123 (1994).

183.R. J. Linderman and M. Jaber, Tetrahedron Lett., 35, 5993 (1994).

184.K. S. Kocchar, D. A. Cottrel and H. W. Pinnick, Tetrahedron Lett., 24, 1323 (1983).

185.R. G. Kuimelis and K. P. Nambiar, Tetrahedron Lett., 34, 3813 (1993).

186.C. Crestini, R. Saladino and R. Nicoletti, Tetrahedron Lett., 34, 1631 (1993).

187.H. Alper, C. Kwiatkowskac, J. F. Petrignani and F. Sibtain, Tetrahedron Lett., 27, 5449 (1986).

188.C. Crestini, R. Saladino, R. Bernini and E. Mincione, Tetrahedron Lett., 34, 7785 (1993).

14. Some synthetic uses of double-bonded functional groups

769

189.W. Adam and B. Nestler, Tetrahedron Lett., 34, 611 (1993).

190.R. S. Coleman and A. J. Carpenter, J. Org. Chem., 58, 4452 (1993).

191.R. S. Coleman and A. J. Carpenter, J. Org. Chem., 57, 5813 (1992).

192.A. Feuerer and T. Severin, J. Org. Chem., 59, 6026 (1994).

193.A. Feuerer and T. Severin, Tetrahedron Lett., 34, 2103 (1993).

194.H. Fischer, M. Klippe, H. Lerche, T. Severin and G. Wanninger, Chem. Ber., 123, 399 (1990).

195.P. Bovonsombat, G. J. Angara and E. Mc Nelis, Tetrahedron Lett., 35, 6787 (1994).

196.M. V. Sargent, J. Chem. Soc., Perkin Trans. 1, 1429 (1990).

197.W. P. Almeida and C. R. D. Correia, Tetrahedron Lett., 35, 1367 (1994).

198.V. K. Singh, Synthesis, 605 (1992).

199.P. H. M. Delanghe and M. Lautens, Tetrahedron Lett., 35, 9513 (1994).

200.Y. B. Xiang, K. Snow and M. Belley, J. Org. Chem., 58, 993 (1993).

201.T. Oishi and T. Nakata, Acc. Chem. Res., 17, 338 (1984).

202.H. Fujita, K. Oshima and K. Utimoto, Tetrahedron Lett., 32, 6147 (1991).

203.M. Taniguchi, H. Fujita, K. Oshima and K. Utimoto, Tetrahedron, 49, 11169 (1993).

204.A. M. P. Koskinen and P. M. Koskinen, Tetrahedron Lett., 34, 6765 (1993).

205.J.-J. Brunet, R. Chauvin, F. Kindela and D. Neibecker, Tetrahedron Lett., 35, 8801 (1994).

206.K. S. Ravikumar, S. Baskaran and S. Chandrasekaran, J. Org. Chem., 58, 5981 (1993).

207.J. P. Versleijen, M. S. Sanders-Hovens, S. A. Vanhommerig, J. A. Vekmans and E. M. Meijer, Tetrahedron, 49, 7793 (1993).

208.G. Wang, T. Heinz, A. Pfaltz, B. Minder, T. Mallat and A. Baiker, J. Chem. Soc., Chem. Commun., 2047 (1994).

209.B. Figadere, C. Chaboche, X. Franck, J.-F. Peyrat and A. Cave, J. Org. Chem., 59, 7138 (1994).

210.I. Shibata, T. Yoshida, T. Kawakami, A. Baba and H. Matsuda, J. Org. Chem., 57, 4049 (1992).

211.E. Vedejs, S. M. Duncan and A. R. Haight, J. Org. Chem., 58, 3046 (1993).

212.T. Kawakami, I. Shibata, A. Baba and H. Matsuda, J. Org. Chem., 58, 7608 (1993).

213.I. Shibata, K. Nakamura, A. Baba and H. Matsuda, Tetrahedron Lett., 31, 6381 (1990).

214.T. Kawakami, I. Shibata, A. Baba and H. Matsuda, J. Org. Chem., 58, 7608 (1993).

215.T. Kawakami, I. Shibata, A. Baba, H. Matsuda and N. Sonoda, Tetrahedron Lett., 35, 8625 (1994).

216.I. Shibata, T. Yoshida, T. Kawakami, A, Baba and H. Matsuda, J. Org. Chem., 57, 4049 (1992).

217.E. Vedejs, S. M. Duncan and A. R. Haight, J. Org. Chem., 58, 3046 (1993).

218.Y. Nishibayashi, J. D. Singh, K. Segawa, S. Fukuzawa and S. Uemura, J. Chem. Soc., Chem. Commun., 1375 (1994).

219.T. Ohkuma, S. Hashiguchi and R. Noyori, J. Org. Chem., 59, 217 (1994).

220.R. L. Halterman, T. M. Ramsey and Z. Chen., J. Org. Chem., 59, 2642 (1994).

221.B. Torok, K. Felfoldi, A. Molnar and M. Bartok, J. Organomet. Chem., 460, 111 (1993).

222.A. Tai, T. Kikukawa, T. Sugimura, Y. Inoue, T. Osawa and S. Fujii, J. Chem. Soc., Chem. Commun., 795 (1990).

223.H. Hata, S. Shimizu, S. Hattori and H. Yamada, J. Org. Chem., 55, 4377 (1990).

224.J. Hoffmann and J. Voss, Elektrochim. Acta, 36, 465 (1991).

225.Y. H. Kim, D. H. Park, I. S. Byun, I. K. Yoon and C. S. Park, J. Org. Chem., 58, 4511 (1993).

226.M. R. Sestrick, M. Miller and L. S. Hegedus, J. Am. Chem. Soc., 114, 4079 (1992).

227.J. Martens, C. Dauelsberg, W. Behnen and S. Wallbaum, Tetrahedron Asymmetry, 3, 347 (1992).

228.J. D. Bloom, M. D. Dutia, B. D. Johnson, A. Wissner, M. G. Burns, E. E. Largis, J. A. Dolan and T. H. Claus, J. Med. Chem., 35, 3081 (1992).

229.A. V. Rama Rao, M. K. Gurjar, P. A. Sharma and V. Kaiwar, Tetrahedron Lett., 31, 2341 (1990).

230.D. J. Mathre, A. S. Thompson, A. W. Douglas, K. Hoogsteen, J. D. Carroll, E. G. Corley and E. J. J. Grabowski, J. Org. Chem., 58, 2880 (1993).

231.S. Wallbaum and J. Martens, Tetrahedron Asymmetry, 2, 1093 (1991).

232.Y. Hong, Y. Gao, X. Nie and C. M. Zepp, Tetrahedron Lett., 35, 6631 (1994).

233.A. V. R. Rao, M. K. Gurjar and V. Kaiwar, Tetrahedron Asymmetry, 3, 859 (1992).

234. M. Labelle,

P. Prasit, M. Belley, M. Blouin, E. Champion, L. Charette,

J. G. DeLuca,

C. Dufresne,

R. Frenette, J. Y. Gauthier, E. Grimm, S. J. Grossman, D. Guay,

E. G. Herold,

T. R. Jones, Y. Lau, Y. Leblanc, S. Leger, A. Lord, M. McAuliffe, C. McFarlane, P. Masson, K. M. Metters, N. Ouimet, D. H. Patrick, H. Perrier, H. Piechuta, P. Roy, H. Williams, Z. Wang, Y. B. Xiang, R. J. Zamboni, A. W. Ford-Hutchinson and R. N. Young, Bioorg. Med. Chem. Lett., 2, 1141 (1992).

770

Jeff Hoyle

235.R. Berenguer, J. Garcia, M. Gonzalez and J. Vilarrasa, Tetrahedron Asymmetry, 4, 13 (1993).

236.K. Tanaka, J. Matsui and H. Suzuki, J. Chem. Soc., Chem. Commun., 1311 (1991).

237.M. P. DeNinno, R. J. Perner, H. E. Morton and S. DiDomenico, J. Org. Chem., 57, 7115 (1992).

238.E. J. Corey, R. K. Bakshi and S. Shibata, J. Org. Chem., 53, 2861 (1988).

239.M. P. DeNinno, R. J. Perner and L. Lijewski, Tetrahedron Lett., 31, 7415 (1990).

240.G. J. Quallich and T. M. Woodall, Tetrahedron Lett., 34, 785 (1993).

241.E. J. Corey and R. K. Bakshi, Tetrahedron Lett., 31, 611 (1990).

242.E. J. Corey and J. O. Link, Tetrahedron Lett., 30, 6275 (1989).

243.B. T. Cho and Y. S. Chun, J. Chem. Soc., Perkin Trans. 1, 3200 (1990).

244.B. T. Cho and Y. S. Chun, Tetrahedron Asymmetry, 3, 337 (1992).

245.R. Romagnoli, E. C. Roos, H. Hiemstra, M. J. Moolenaar and W. N. Speckamp, Tetrahedron Lett., 35, 1087 (1994).

246.S. Itsuno, M. Nakano and K. Ito, J. Chem. Soc., Perkin Trans. 1, 2615 (1985).

247.C. Bolm and M. Felder, Tetrahedron Lett., 34, 6041 (1993).

248.J. S. Cha, S. J. Min, J. M. Kim, O. O. Kwon and M. K. Jeoung, Org. Prep. Proc. Int., 25, 466 (1993).

249.Y.-J. Shi, D. Cai, U.-H. Dolling, A. W. Douglas, D. M. Tschaen and T. R. Verhoeven, Tetrahedron Lett., 35, 6409 (1994).

250.R. J. Mears and A. Whiting, Tetrahedron Lett., 34, 8155 (1993).

251.G. A. Molnder, K. L. Bobbitt and C. K. Murray, J. Am. Chem. Soc., 114, 2759 (1992).

252.B. T. Cho and Y. S. Chun, Tetrahedron Asymmetry, 5, 1147 (1994).

253.G. A. Molander and K. L. Bobbitt, J. Am. Chem. Soc., 115, 7518 (1993).

254.C. L. Raston, A. F. H. Siu, C. J. Tranter and D. J. Young, Tetrahedron Lett., 35, 5915 (1994).

255.C. J. Sih and C.-S. Chen, Angew. Chem., Int. Ed. Engl., 23, 570 (1984).

256.S. Servi, Synthesis, 1 (1990).

257.R. Cusk and B. I. Glanzer, Chem. Rev., 91, 49 (1991).

258.K. Ishihara, T. Sakai, S. Tsuboi and M. Utaka, Tetrahedron Lett., 35, 4569 (1994).

259.K. Nakamura, K. Inoue, K. Ushio, S. Oka and A. Ohno, J. Org. Chem., 53, 2598 (1988).

260.D. Zakarya, L. Farhaoui and S. Fkih-Tetouani, Tetrahedron Lett., 35, 4985 (1994).

261.G. Pedrocchi-Fantoni, S. Redaelli, S. Servi and H.-E. Hogberg, Gazz. Chim. Ital., 122, 499 (1992).

262.J. Kearns and M. M. Kayser, Tetrahedron Lett., 35, 2845 (1994).

263.B. K. Sarmah and N. C. Barua, Tetrahedron, 49, 2253 (1993).

264.R. Csuk and B. I. Glanzer, Chem. Rev., 91, 2567 (1991).

265.E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 92, 1071 (1992).

266.J. Cooper, P. T. Gallgher and D. W. Knight, J. Chem. Soc., Chem. Commun., 1313 (1993).

267.M. H. Ansari, T. Kusumoto and T. Hiyama, Tetrahedron Lett., 34, 8271 (1993).

268.L. Y. Jayasinghe, A. J. Smallridge and M. A. Trewhella, Tetrahedron Lett., 34, 3949 (1993).

269.B. Patro, B. Deb, H. Ila and H. Junjappa, J. Org. Chem., 57, 2257 (1992).

270.B. Deb, H. Ila and H. Junjappa, J. Chem. Res. (S), 356 (1990).

271.B. Deb, H. Ila and H. Junjappa, J. Chem. Res. (M), 2728 (1990).

272. K. Mashima, K. Kusano, N. Sato, Y. Matsumura, K. Nozaki, H. Kumobayashi, N. Sayo,

Y. Hori, T. Ishizaki, S. Akutagawa and H. Takaya, J. Org. Chem., 59, 3064 (1994).

273.Y. Kawai, M. Tsujimoto, S. Kondo, K. Takanobe, K. Nakamura and A. Ohno, Bull. Chem. Soc. Jpn., 67, 524 (1994).

274.Y. Kawai, S. Kondo, M. Tsujimdo, K. Nakamura and A. Ohno, Bull. Chem. Soc. Jpn., 67, 2244 (1994).

275.K. Nakamura, Y. Inoue, J. Shibahara and A. Ohno, Bull. Inst. Chem. Res., Kyoto Univ., 67, 99 (1989).

276.T. Hafner and H. U. Ressig, Justus Liebigs Ann. Chem., 937 (1989).

277.F. Felluga, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 123, 443 (1993).

278.M. Takeshita, R. Yaguchi and N. Akutsu, Tetrahedron Asymmetry, 3, 1369 (1992).

279.M. Takeshita and N. Akutsu, Tetrahedron Asymmetry, 3, 1381 (1992).

280.M. Takeshita, M. Miura and Y. Unuma, J. Chem. Soc., Perkin Trans. 1, 2901 (1993).

281.T. Izumi and K. Fukaya, Bull. Chem. Soc. Jpn., 66, 1216 (1993).

282.K. Mori, Bull. Soc. Chim. Belg., 101, 393 (1992).

283.H. Watanabe and K. Mori, J. Chem. Soc., Chem. Commun., 2919 (1991).

284.K. Mori and E. Nagano, Biocatalysis, 3, 25 (1990).

14. Some synthetic uses of double-bonded functional groups

771

285.K. Mori, S. Takayama and S. Yoshimura, Justus Liebigs Ann. Chem., 91 (1993).

286.V. Waagen, V. Partali, I. Hollingsaeter, M. S. S. Huang and T. Anthonsen, Acta Chem. Scand., 48, 506 (1994).

287.P. Ferraboschi, P. Grisenti, A. Manzocchi and E. Santaniello, Tetrahedron, 50, 10539 (1994).

288.P. Ferraboschi, P. Grisenti, A. Manzocchi and E. Santaniello, J. Chem. Soc., 2469 (1990).

289.T. Sato and T. Fujisawa, Biocatalysis, 3, 1 (1990).

290.A. Forni, I. Moretti, F. Prati and G. Torre, Tetrahedron, 50, 11995 (1994).

291.U. T. Bhalerao, L. Dasaradhi, C. Muralikrishna and N. W. Fadnavis, Tetrahedron Lett., 34, 2359 (1993).

292.M. J. Burk, T. G. P. Harper, J. R. Lee and C. Kalberg, Tetrahedron Lett., 35, 4963 (1994).

293.T. Chiba, A. Miyashita, H. Nohira and H. Takaya, Tetrahedron Lett., 34, 2351 (1993).

294.P. R. Guzzo and M. J. Miller, J. Org. Chem., 59, 4862 (1994).

295.T. Ohta, T. Tsutsumi and H. Takaya, J. Organomet. Chem., 484, 191 (1994).

296.J. B. Hoke, L. S. Hollis and E. W. Stern, J. Organomet. Chem., 455, 193 (1993).

297. X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima and

H. Takaya, J. Am. Chem. Soc., 115, 3318 (1993).

298.S. Gladiali, L. Pinna, G. Delogu, E. Graf and H. Brunner, Tetrahedron Asymmetry, 1, 937 (1990).

299.S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich and G. Mestroni, Tetrahedron Asymmery, 1, 635 (1990).

300.P. Gamez, F. Fache, P. Mangeney and M. Lemaire, Tetrahedron Lett., 34, 6897 (1993).

301.P. Gamez, B. Dunjic, F. Fache and M. Lemaire, J. Chem. Soc., Chem. Commun., 1417 (1994).

302.G. Zassinovich, G. Mestroni and S. Gladiali, Chem. Rev., 92, 1051 (1992).

303.D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Yang and D. Hunziger, Helv. Chim. Acta, 75, 2171 (1992).

304.D. A. Evans, S. G. Nelson, M. R. Gagne and A. R. Muci, J. Am. Chem. Soc., 115, 9800 (1993).

305.A. Lebrun, J. L. Namy and H. B. Kagan, Tetrahedron Lett., 32, 2355 (1991).

306.M. Shibagaki, K. Takahashi, H. Kuno and H. Matsushita, Bull. Chem. Soc. Jpn., 63, 258 (1990).

307.K. Inada, M. Shibagaki, Y. Nakanishi and H. Matsushita, Chem. Lett., 1795 (1993).

308.M. Bordoloi, Tetrahedron Lett., 34, 1681 (1993).

309.S. Singh and S. Dev, Tetrahedron, 49, 10959 (1993).

310.T. Tsukinoki, K. Ishimoto, H. Tsuzuki, S. Mataka and M. Tashiro, Bull. Chem. Soc. Jpn., 66, 3419 (1993).

311.M. K. Das, P. K. Maiti and A. Bhaumik, Bull. Chem. Soc. Jpn., 66, 810 (1993).

312.T. Kawate, M. Nakagawa, T. Kakikawa and T. Hino, Tetrahedron Asymmetry, 3, 227 (1992).

313. H. O. House, Modern Synthetic Reactions, W. A. Benjamin, Menlo Park, California, 1972,

pp. 73 77, 210 13.

314.R. Balicki and L. Kaczmarek, Gazz. Chim. Ital., 123, 525 (1993).

315.C. A. Willoughby and S. L. Buchwald, J. Org. Chem., 58, 7627 (1993).

316.A. R. Pinder, Nat. Prod. Rep., 9, 17 (1992).

317.M. J. Burk and J. E. Feaster, J. Am. Chem. Soc., 114, 7266 (1992).

318.A. G. Becalski, W. R. Cullen, M. D. Fryzuk, B. R. James, G.J. Kand and S. J. Rettig, Inorg. Chem., 30, 5002 (1991).

319.C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 114, 7562 (1992).

320.Y. N. C. Chan and J. A. Osborn, J. Am. Chem. Soc., 112, 9400 (1990).

321.J. Bakos, A. Orosz, B. Heil, M. Laghmari, P. Lhoste and D. Sinou, J. Chem. Soc., Chem. Commun., 1684 (1991).

322.T. Kawate, M. Nakagawa, T. Kakikawa and T. Hino, Tetrahedron Asymmetry, 3, 227 (1992).

323.F. Spindler, B. Pugin and H. U. Blaser, Angew. Chem., Int. Ed. Engl., 29, 558 (1990).

324.H. Ahlbrecht and V. Baumann, Synthesis, 770 (1994).

325.N. De Kimpa and E. Stanoeva, Synthesis, 695 (1994).

326.N. Khiar, I. Fernandez, F. Alcudia and D. H. Hua, Tetrahedron Lett., 34, 699 (1993).

327.J. C. Fuller, E. L. Stangeland, C. T. Goralski and B. Singaram, Tetrahedron Lett., 34, 257 (1993).

328.G. B. Fisher, J. C. Fuller, J. Harrison, C. T. Goralski and B. Singaram, Tetrahedron Lett., 34, 1091 (1993).

329.J. C. Fuller, C. M. Belisle, C. T. Goralski and B. Singaram, Tetrahedron Lett., 35, 5389 (1994).

330.B. Lejczak, P. Kafarski and J. Zygmunt, Biochemistry, 28, 3459 (1989).

331.D. Green, G. Patel, S. Elgendy, J. A. Baban, G. Claeson, V. V. Kakkar and J. Deadman, Tetrahedron Lett., 34, 6917 (1993).

772

Jeff Hoyle

332.Y. Hong, Y. Gao, X. Nie and C. M. Zepp, Tetrahedron Lett., 35, 5551 (1994).

333.C. K. Miao, R. Sorcek and P. J. Jones, Tetrahedron Lett., 34, 2259 (1993).

334.R. D. Broene and S. L. Buchwald, J. Am. Chem. Soc., 115, 12569 (1993).

335.I. Ojima, N. Clos and C. Bastos, Tetrahedron, 45, 6901 (1989).

336.R. Noyori, Science, 248, 1194 (1990).

337.A. Pfaltz, Acc. Chem. Res., 26, 339 (1993).

338.H. Takaya, T. Ohta and R. Noyori, in Catalytic Asymmetric Synthesis (Ed. I. Ojima), VCH, New York, 1993, pp. 1 39.

339.T. Cuenca, J. C. Flores and P. Royo, J. Organomet. Chem., 462, 191 (1993).

340.T. Manimaran, T-C. Wu, W. D. Klobucar, C. H. Kolich and G. P. Stahly, Organometallics, 12, 1467 (1993).

341.R. L. Halterman, K. P. C. Vollhardt, M. E. Welker, D. Blaser and R. Boese, J. Am. Chem. Soc., 109, 8105 (1987).

342.R. L. Halterman and K. P. C. Vollhardt, Organometallics, 7, 883 (1988).

343.K. Wan and M. E. Davis, J. Chem. Soc., Chem. Commun., 1262 (1993).

344.M. J. Burk, J. E. Feaster, W. A. Nugent and R. L. Harlow, J. Am. Chem. Soc., 115, 10125 (1993).

345.M. Lautens, C. H. Zhang, B. J. Goh, C. M. Crudden and M. J. A. Johnson, J. Org. Chem., 59, 6208 (1994).

346.T. Masquelin, E. Broger, K. Muller, R. Schmid and D. Obrecht, Helv. Chim. Acta, 77, 1395 (1994).

347.T. Pham and W. D. Lubell, J. Org. Chem., 59, 3676 (1994).

348.A. Borner, J. Ward, W. Ruth, J. Holz, A. Kless, D. Heller and H. B. Kagan, Tetrahedron, 50, 10419 (1994).

349.M. J. Burk and M. F. Gross, Tetrahedron Lett., 35, 9363 (1994).

350.M. J. Burk, J. R. Lee and J. P. Martinez, J. Am. Chem. Soc., 116, 10847 (1994).

351.X. Zhang, T. Uemura, K. Matsumura, N. Sayo, H. Kumobayashi and H. Takaya, Synlett, 501 (1994).

352.G. Beck, H. Jendralla and B. Kammermeier, Tetrahedron, 50, 4691 (1994).

353.J. K. Nielsen and J. O. Madsen, Tetrahedron Asymmetry, 5, 403 (1994).

354.E. Juaristi, A. K. Beck, J. Hansen, T. Matt, T. Mukhopadhyay, M. Simson and D. Seebach, Synthesis, 1271 (1993).

355.J. Gonda, A.-C. Helland, B. Ernst and D. Bellus, Synthesis, 729 (1993).

356.C. Narayana and M. Periasamy, Synthesis, 253 (1985).

357.H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation. Direct Synthesis of Carbonyl Compounds. Plenum Press, New York, 1991.

358.B. El Ali and H. Alper, J. Org. Chem., 58, 3595 (1993).

359.T. Mandai, Y. Tsujiguchi, S. Matsuoka, J. Tsuji and S. Saito, Tetrahedron Lett., 35, 5697 (1994).

360.B. El Ali and H. Alper, J. Mol. Catal., 77, 7 (1992).

361.T. Mandai, Y. Tsujiguchi, J. Tsuji and S. Saito, Tetrahedron Lett., 35, 5701 (1994).

362.B. El Ali, G. Vasapollo and H. Alper, J. Org. Chem., 58, 4739 (1993).

363.J. N. Freskos, S. A. Laneman, M. L. Reilly and D. H. Ripin, Tetrahedron Lett., 35, 835 (1994).

364.J. M. Baird, R. J. Kern, R. G. Lee, D. J. Morgans and M. L. Spavacino, J. Org. Chem., 56, 1928 (1991).

365.H. Alper and N. Hamel, J. Am. Chem. Soc., 112, 2803 (1990).

366.I. Ryu and H. Alper, J. Am. Chem. Soc., 115, 7543 (1993).

367.R. Takeuchi and M. Sugiura, J. Chem. Soc., Perkin Trans. 1, 1031 (1993).

368.H. Arzoumanian, F. Cochini, D. Nuel and N. Rosas, Organometallics, 12, 1871 (1993).

369.I. Ryu, H. Yamazaki, A. Ogawa, N. Kambe and N. Sonoda, J. Am. Chem. Soc., 115, 1187 (1993).

370.I. Ryu, M. Hasegawa, A. Kurihara, A. Ogawa, S. Tsunoi and N. Sonoda, Synlett, 143 (1993).

371.N. E. Schore, Chem. Rev., 88, 1081 (1988).

372.N. E. Schore, Org. React., 40, 1 (1991).

373.D. L. J. Clive, D. C. Cole and Y. Tao, J. Org. Chem., 59, 1396 (1994).

374.T. R. Hoye and J. A. Suriano, J. Am. Chem. Soc., 115, 1154 (1993).

375.M. E. Krafft and C. Wright, Tetrahedron Lett., 33, 151 (1992).

376.M. E. Krafft, R. H. Romero and I. L. Scott, J. Org. Chem., 57, 5277 (1992).

377.M. E. Krafft and C. A. Juliano, J. Org. Chem., 57, 5106 (1992).

378.N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee and S. Yoo, Synlett, 204 (1991).

379.S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 31, 5289 (1990).

14. Some synthetic uses of double-bonded functional groups

773

380.Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek and P. L. Pauson, Organometallics, 12, 220 (1993).

381.N. Jeong, S. H. Hwang and Y. Lee, J. Am. Chem. Soc., 116, 3159 (1994).

382.M. E. Krafft, I. L. Scott, R. H. Romero, S. Feibelmann and C. E. Van Pelt, J. Am. Chem. Soc., 115, 7199 (1993).

383.S. Yoo and S. H. Lee, J. Org. Chem., 59, 6968 (1994).

384.J. Marco-Contelles, Tetrahedron Lett., 35, 5059 (1994).

385.M. E. Krafft and X. Chirico, Tetrahedron Lett., 35, 4511 (1994).

386.K. Totland and H. Alper, J. Org. Chem., 58, 3326 (1993).

387.G. C. Cuny and S. L. Buchwald, J. Am. Chem. Soc., 115, 2066 (1993).

388.E. Fernandez and S. Castillon, Tetrahedron Lett., 35, 2361 (1994).

389.K. Yamamoto, S. Momose, M. Funahashi, S. Ebata, H. Ohmura, H. Komatsu and M. Miyazawa, Chem. Lett., 189 (1994).

390.E. M. Campi, W. R. Jackson, P. Perlmutter and E. E. Tasdelen, Aust. J. Chem., 46, 995 (1993).

391.C. M. Crudden and H. Alper, J. Org. Chem., 59, 3091 (1994).

392.T. J. Kwok and D. J. Wink, Organometallics, 12, 1954 (1993).

393.G. Vasapollo, A. Somasunderam, B. El Ali and H. Alper, Tetrahedron Lett., 35, 6203 (1994).

394.I. Ryu, A. Kurihara, H. Muraoka, S. Tsunoi, N. Kambe and N. Sonoda, J. Org. Chem., 59, 7570 (1994).

395.R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.

396.E. I. Negishi, M. Ay, Y. V. Gulevich and Y. Noda, Tetrahedron Lett., 34, 1437 (1993).

397.A. R. De Lera, A. Torrado, B. Iglesias and S. Lopez, Tetrahedron Lett., 33, 6205 (1992).

398.F. Ozawa, Y. Kobatake, A. Kubo and T. Hayashi, J. Chem. Soc., Chem. Commun., 1323 (1994).

399.E. I. Negishi and Z. Owczarczyk, Tetrahedron Lett., 32, 6683 (1991).

400.H. Bienayme and C. Yezeguelian, Tetrahedron Lett., 35, 3389 (1994).

401.G. T. Crisp and P. T. Glink, Tetrahedron, 50, 2623 (1994).

402.K. Voigt, U. Schick, F. E. Meyer and A. De Meijere, Synlett, 189 (1994).

403.S. Hatakeyama, H. Irie, T. Shintani, Y. Noguchi, H. Yamada and M. Nishizawa, Tetrahedron, 50, 13369 (1994).

404.J. L. Mascarenas, A. M. Garcia, L. Castedo and A. Mourino, Tetrahedron Lett., 33, 4365 (1992).

405.Q. Zheng, Y. Yang and A. R. Martin, Tetrahedron Lett., 34, 2235 (1993).

406.C. R. Johnson and M. P. Braun, J. Am. Chem. Soc., 115, 11014 (1993).

407.D. Janietz and M. Bauer, Synlett, 33 (1993).

408. C. R. Johnson, J. P. Adam, M. P. Braun, C. B. W. Senanayake, P. M. Wovkulich and

M.R. Uskokovic, Tetrahedron Lett., 33, 917 (1992).

409.J. A. Soderquist and J. C. Colberg, Tetrahedron Lett., 35, 27 (1994).

410.A. Suzuki, Pure Appl. Chem., 63, 419 (1991).

411.W.-C. Shieh and J. A. Carlson, J. Org. Chem., 57, 379 (1992).

412.R. Rossi, F. Bellina, A. Carpita, D. Ciucci and M. De Santis, Tetrahedron, 49, 4677 (1993).

413.C. R. Johnson, J. P. Adams, M. P. Braun and CBW Senanayake, Tetrahedron Lett., 33, 919 (1992).

414.E. Negishi, Z. Owczarczyk and D. Swanson, Tetrahedron Lett., 32, 4453 (1991).

415.K. A. Agrios and M. Srebnik, J. Org. Chem., 59, 5468 (1994).

416.H. Stadtmuller, R. Lentz, C. E. Tucker, T. Studemann, W. Dorner and P. Knochel, J. Am. Chem. Soc., 115, 7027 (1993).

417.E. Negishi, M. D. Jensen, D. Y. Kondakov and S. Wang, J. Am. Chem. Soc., 116, 8404 (1994).

418.M. Kanai and K. Tomioka, Tetrahedron Lett., 35, 895 (1994).

419.A. Alexakis, S. Mutti and J. F. Normant, J. Am. Chem. Soc., 113, 6332 (1991).

420.G. H. Grant and S. V. Ley, Tetrahedron Lett., 35, 7455 (1994).

421.K. Tomioka, T. Suenaga and K. Koga, Tetrahedron Lett., 27, 369 (1986).

422.B. E. Rossiter, M. Eguchi, G. Miao, N. M. Swingle, A. E. Hernandez, D. Vickers, E. Fluckiger,

R.G. Patterson and K. V. Reddy, Tetrahedron, 49, 965 (1993).

423.F. Lambert, D. M. Knotter, M. D. Janssen, M. Van Klaveren, J. Boersma and G. Van Koten,

Tetrahedron Asymmetry, 2, 1097 (1991).

424.K. Tanaka, J. Matsui, K. Somemiya and H. Suzuki, Synlett, 351 (1994).

425.M. Van Klaveren, F. Lambert, D. J. F. M. Eijkelkamp, D. M. Grove and G. Van Koten, Tetrahedron Lett., 35, 6135 (1994).

426.K.-H. Ahn, R. B. Klassen and S. J. Lippard, Organometallics, 9, 3178 (1990).

774

Jeff Hoyle

427.B. E. Rossiter and N. M. Swingle, Chem. Rev., 92, 771 (1992).

428.K. Tomioka, Synthesis, 541 (1990).

429.M. Mori, N. Uesaka and M. Shibasaki, J. Chem. Soc., Chem. Commun., 1222 (1990).

430.M. Mori, N. Uesaka and M. Shibasaki, J. Org. Chem., 57, 3519 (1992).

431.K. S. Knight and R. M. Waymouth, J. Am. Chem. Soc., 113, 6268 (1991).

432.T. Takahashi, T. Seki, Y. Nitto, M. Saburi, C. J. Rousset and E. Negishi, J. Am. Chem. Soc., 113, 6266 (1991).

433.D. F. Taber, J. P. Louey and J. A. Lim, Tetrahedron Lett., 34, 2243 (1993).

434.A. H. Hoveyda and J. P. Morken, J. Org. Chem., 58, 4237 (1993).

435.M. Watanabe and K Soai, J. Chem. Soc., Perkin Trans. 1, 3125 (1994).

436.B. T. Cho and N. Kim, Tetrahedron Lett., 35, 4115 (1994).

437.K. Soai and S. Niwa, Chem. Rev., 92, 833 (1992).

438.C. Dreisbach, U. Kragl and C. Wandrey, Synthesis, 911 (1994).

439.H. Waldmann, M. Weigerding, C. Dreisbach and C. Wandrey, Helv. Chim. Acta, 77, 2111 (1994).

440.Y. N. Ito, X. Ariza, A. K. Beck, A. Bohac, C. Ganter, R. E. Gawley, F. N. M. Kuhnle, J. Tuleja, Y. M. Wang and D. Seebach, Helv. Chim. Acta, 77, 2071 (1994).

441.J. Kang, J. W. Kim and J. I. Kim, J. Chem. Soc., Chem. Commun., 2009 (1994).

442.E. Rijnberg, J. T. B. H. Jastrzebski, M. D. Janssen, J. Boersma and G van Koten, Tetrahedron Lett., 35, 6521 (1994).

443.J. Kang, D. S. Kim and J. I. Kim, Synlett, 842 (1994).

444.M. Ishizaki and O. Hoshino, Chem. Lett., 1337 (1994).

445.K. Soai and K. Takahashi, J. Chem. Soc., Perkin Trans. 1, 1257 (1994).

446.S. Vettel and P. Knochel, Tetrahedron Lett., 35, 5849 (1994).

447.C. Eisenberg and P. Knochel, J. Org. Chem., 59, 3760 (1994).

448.R. Ostwald, P.-Y. Chavant, H. Stadtmuller and P. Knochel, J. Org. Chem., 59, 4143 (1994).

449.L. Schwink and P. Knochel, Tetrahedron Lett., 35, 9007 (1994).

450.M. J. Rozema, C. Eisenberg, H. Lutjens, R. Ostwald, K. Belyk and P. Knochel, Tetrahedron Lett., 34, 3115 (1993).

451.M. J. Rozema, S. Achyutha Rao and P. Knochel, J. Org. Chem., 57, 1956 (1992).

452.W. Oppolzer and R. N. Radinov, Tetrahedron Lett., 32, 5777 (1991).

453.W. Oppolzer and R. N. Radinov, Helv. Chim. Acta, 75, 170 (1992).

454.B. Weber and D. Seebach, Angew. Chem., Int. Ed. Engl., 31, 84 (1991).

455.J. L. Bussche-Hunnefeld and D. Seebach, Tetrahedron, 48, 5719 (1992).

456.R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 1321 (1990).

457.G. Zadel and E. Breitmaier, Chem. Ber., 127, 1323 (1994).

458.U. Koert, M. Stein and K. Harms, Angew. Chem., Int. Ed. Engl., 33, 1180 (1994).

459.U. Koert, M. Stein and K. Harms, Tetrahedron Lett., 34, 2229 (1993).

460.T. R. Hoye and P. Hanson, Tetrahedron Lett., 34, 5043 (1993).

461.J. C. Harmange and B. Figadere, Tetrahedron Asymmetry, 4, 1711 (1993).

462.S. C. Sinha and E. Keinan, J. Am. Chem. Soc., 115, 4891 (1993).

463.B. Figadere, J. C. Harmange, L. X. Hai and A. Cave, Tetrahedron Lett., 33, 5189 (1992).

464.U. Koert, Tetrahedron Lett., 35, 2517 (1994).

465.U. Koert, H. Wagner and U. Pidun, Chem. Ber., 127, 1447 (1994).

466.A. Yanagisawa, S. Habaue, K. Yasue and H. Yamamoto, J. Am. Chem. Soc., 116, 6130 (1994).

467.Y. Hashimoto, H. Kagoshima and K. Saigo, Tetrahedron Lett., 35, 4805 (1994).

468.P. Ciapetti, M. Taddei and P. Ulivi, Tetrahedron Lett., 35, 3183 (1994).

469.S. E. Denmark, D. M. Coe, N. E. Pratt and B. D. Griedel, J. Org. Chem., 59, 6161 (1994).

470.S. Kobayashi and K. Nishio, J. Org. Chem., 59, 6620 (1994).

471.S. J. Stanway and E. J. Thomas, J. Chem. Soc., Chem. Commun., 285 (1994).

472.W. R. Roushand, M. S. VanNieuwenhze, J. Am. Chem. Soc., 116, 8536 (1994).

473.H. C. Aspinall, A. F. Browning, N. Greeves and P. Ravenscroft, Tetrahedron Lett., 35, 4639 (1994).

474.A. H. McNeill and E. J. Thomas, Synthesis, 322 (1994).

475.Y. Nishigaichi, M. Fujimoto and A. Takuwa, Synlett, 731 (1994).

476.J. Ipaktschi, A. Heydari and H.-O. Kalinowski, Chem. Ber., 127, 905 (1994).

477.H. C. Brown, U. R. Khire and U. S. Racherla, Tetrahedron Lett., 34, 15 (1993).

478.F. Roux, I. Maugras, J. Poncet, G. Niel and P. Jouin, Tetrahedron, 50, 5345 (1994).

479.G. Niel, F. Roux, Y. Maisonnasse, I. Maugras, J. Poncet and P. Jouin, J. Chem. Soc., Perkin Trans. 1, 1275 (1994).

Соседние файлы в папке Patai S., Rappoport Z. 1997 The chemistry of functional groups. The chemistry of double-bonded functional groups