Скачиваний:
28
Добавлен:
15.08.2013
Размер:
665.11 Кб
Скачать

19. Electrophilic additions to double bonds

1215

186.H. Masuda, K. Takahase, M. Nishio, A. Hasegawa, Y. Nishiyama and Y. Ishii, J. Org. Chem., 59, 5550 (1994).

187.G. Bellucci, R. Bianchini and C. Chiappe, J. Org. Chem., 56, 3067 (1991).

188.W. B. Smith and B. D. Mercer, J. Org. Chem., 53, 127 (1988).

189.F. Radner, Acta Chem. Scand., 43, 902 (1989).

190. V. L. Heasley, B. R. Berry, S. L. Holmes, L. S. Holstein, K. A. Milhoan, A. M. Sauerbrey,

B.R. Teegarden and D. F. Shellhammer, J. Org. Chem., 53, 198, (1988).

191.V. L. Healsley, L. S. Holstein, R. J. Moreland, J. W. Rosbrugh and D. F. Shellhamer, J. Chem. Soc., Perkin Trans. 2, 127 (1991).

192.D. Horton, W. Priebe and M. Sznaidman, Carbohyd. Res., 205, 71 (1990).

193.P. Crotti, M. Chini, G. Veccello-Barretta and F. Macchia, J. Org. Chem., 54, 4525 (1989).

194.J. E. Baldwin and Y. Yamaguchi, Tetrahedron Lett., 30, 3335 (1989).

195.Yu. V. Norseev, L. Vasaras, D. D. Nhan and N. K. Juan, Radiokhimiya, 29, 474 (1987); Chem. Abstr., 109, 92032 (1988).

196.J. Sperka and D. C. Liotta, Heterocycles, 35, 701 (1993); Chem. Abstr., 120, 163078 (1994).

197.P. Kocovskˇy´ and M. Pour, J. Org. Chem., 55, 5580 (1990).

198.P. Kocovskˇy,´ V. Langer and A. Gogoll, J. Chem. Soc., Chem. Commun., 1026 (1990).

199.A. Goosen, E. Hoffmann and B. Taljaard, J. Chem. Soc., Perkin Trans 1, 41 (1994).

200.For related reports, see:

(a)L. Mangoni, M. Adinolfi, G. Barone and M. Parrilli, Tetrahedron Lett., 4485. (1973).

(b)M. Parilli, G. Barone, M. Adinolfi and L. Mangoni, Gazz. Chim. Ital., 104, 835 (1974).

201.B. Borhan, S. Nazarin, E. M. Stocking, B. D. Hammock and M. Kurth, J. Org. Chem., 59, 4316 (1994).

202.For a similar strategy, reported earlier, see:

ˇ

(a) P. Kocovskˇy,´ V. Cerny´ and F. Turecek,ˇ Collect. Czech. Chem. Commun., 44, 234 (1979).

(b) P. Kocovskˇy,´ I. Stary´ and F. Turecek,ˇ Tetrahedron Lett., 27, 1513 (1986).

203. N. A. Yashnikova, I. P. Kupchik and V. I. Staninets, Ukr. Khim. Zh., 56, 1301 (1990); Chem. Abstr., 115, 28450 (1991).

204. Y. G. Kim and J. K. Cha, Tetrahedron Lett., 29, 2011 (1988).

205. M. Labelle, H. E. Morton, Y. Guindon and J. P. Springer, J. Am. Chem. Soc., 110, 4533 (1988). 206. F. Freeman and K. D. Robarge, J. Org. Chem., 54, 346 (1989).

207. B. H. Lipshutz and J. C. Barton, J. Am. Chem. Soc., 114, 1084 (1992).

208. E. D. Mihelich and G. A. Hite, J. Am. Chem. Soc., 114, 7318 (1992).

209. J. M. Barks, D. W. Knight, C. J. Seaman and G. G. Weingarten, Tetrahedron Lett., 35, 7259 (1994).

210. J. M. Barks, D. W. Knight and G. G. Weingartenn, J. Chem. Soc., Chem. Commun., 719 (1994). 211. For earlier reports on the seemingly anti-Baldwin 5-endo-Trig cyclization, see e.g. Reference 197

ˇ

and references cited therein; and: P. Kocovskˇy´ and V. Cerny,´ Collect. Czech. Chem. Commun., 43, 1924 (1978).

212.K. Miyashita, A. Tanaka, H. Mizuno, M. Tanaka and C. Iwata, J. Chem. Soc., Perkin Trans. 1, 847 (1994).

213.Y. Tamaru, H. Harayama and T. Bando, J. Chem. Soc., Chem. Commun., 1601 (1993).

214.T. Nishiyama, K. Kitano, H. Kishi and F. Yamada, Bull. Chem. Soc. Jpn., 66, 3822 (1994).

215.R. Rodebaugh and B. Fraser-Reid, J. Am. Chem. Soc., 116, 3155 (1994).

216.A. J. Bennet, R. S. Brown, R. E. D. McClung, M. Klobukowski, G. H. M. Aarts, B. D. Santasiero, G. Bellucci and R. Bianchini, J. Am. Chem. Soc., 113, 8537 (1991).

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

218.Y. Tamaru, H. Harayama and T. Bando, J. Chem. Soc., Chem. Commun., 1601 (1993).

219.S. Yakano, Y. Iwabuchi and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1527 (1988).

220.S. H. Kang and S. B. Lee, Tetrahedron Lett., 34, 1955 (1993).

221.R. W. Friesen, A. Giroux and K. L. Cook, Tetrahedron Lett., 34, 5983 (1993).

222.M. J. Kurth, E. G. Brown, E. J. Lewis and J. C. McKew, Tetrahedron Lett., 29, 1517 (1988).

223.O. Kitagawa, T. Sato and T. Taguchi, Chem. Lett., 177 (1991).

224.M. J. Kurth, R. L. Beard, M. Olmstead and J. G. MacMillan, J. Am. Chem. Soc., 111, 3712 (1989).

225.S. Najdi and M. J. Kurth, Tetrahedron Lett., 31, 3279 (1990).

226.K. Fuji, M. Node, Y. Naniwa and T. Kawabata, Tetrahedron Lett., 31, 3175 (1990).

227.T. Yokomatsu, H. Iwasawa and S. Shibuya, J. Chem. Soc., Chem. Commun., 728 (1992).

1216

Pavel Kocovskˇy´

228.M. Mehlfuhrer,¨ H. Berner and K. Thirring, J. Chem. Soc., Chem. Commun., 1291 (1994).

229.H. Takahaka, Y. Uchida and T. Momose, J. Org. Chem., 59, 7201 (1994).

230.E. Marotta, B. Piombi, P. Righi and G. Rosini, J. Org. Chem., 59, 7526 (1994).

231.R. W. Hoffman, R. Sturmer¨ and K. Harms, Tetrahedron Lett., 35, 6263 (1994).

232.J. Bange, A. F. Haughan and J. B. Sweeney, Tetrahedron Lett., 35, 1405 (1994).

233.J. Font, A. Garcia and P. de March, Tetrahedron, 46, 4407 (1990).

234. N. S. Zefirov, A. S. Koz’min, T. Kasumov, K. A. Potekhin, V. D. Sorokin, V. K. Brel, E. V. Abramkin, Yu. T. Struchkov, V. V. Zhdankin and P. J. Stang, J. Org. Chem., 57, 2433 (1992).

235.R. D. Walkup, L. Guan, S. W. Kim and Y. S. Kim, Tetrahedron Lett., 33, 3969 (1992).

236.R. D. Walkup and G. Park, Tetrahedron Lett., 28, 1023 (1987).

237.R. D. Walkup and G. Park, J. Am. Chem. Soc., 112, 1597, 5388 (1990).

238.R. W. Friesen and A. E. Kolaczewska, J. Org. Chem., 56, 4888 (1991).

´´ ´

239.E. Alvarez, M. T. Diaz, M. L. Rodriguez and J. D. Martin, Tetrahedron Lett., 31, 1629 (1990).

´´ ´

240.M. Zarraga,´ E. Alvarez, J. L. Ravelo, V. Rodriguez, M. L. Rodriguez and J. D. Martin, Tetrahedron Lett., 31, 1633 (1990).

241.P. Kocovskˇy´ and I. Stieborova,´ Tetrahedron Lett., 30, 4295 (1989).

242.A. V. Khotkevich, Yu. A. Serguchev, P. A. Krasutskii, O. V. Kamenskii and A. G. Yurchenko, Teor. Exp. Khim., 25, 249 (1989); Chem. Abstr., 111, 193874 (1989).

243.A. A. Bobylyova, N. F. Dubitskaya, A. V. Khoroshutkin, T. I. Pekh and N. A. Belikova, Tetrahedron Lett., 32, 6429 (1991).

244.M. Oki, K. Maeda, T. Akinaga, Y. Kataoka and S. Toyota, Bull. Chem. Soc. Jpn., 67, 2825 (1994).

245.A. M. Shestopalov, L. A. Rodinovskaya, Yu. A. Sharanin and V. P. Litvinov, Khim. Geterotsikl. Soedin., 256 (1990); Chem. Abstr., 113, 39658 (1990).

246.V. Faivre, C. Lila, A. Sarol and A. Doutheau, Tetrahedron, 45, 7765 (1989).

247.C. F. Palmer, K. P. Parry, S. M. Roberts and V. Sik, J. Chem. Soc., Perkin Trans. 1, 1021 (1992).

248.

´

´

P. Kocovskˇy,´ I. Stary,´ J. Zajicek,ˇ F. Turecekˇ and S. Vasˇickovˇa,´ J. Chem. Soc., Perkin Trans. 1,

 

2297 (1996).

 

249.

B. L. Kam and N. J. Oppenheimer, J. Org. Chem., 46, 3268 (1981).

250.

V. Lucchini, G. Modena and L. Pasquato, J. Chem. Soc., Chem. Commun., 293 (1992).

251.

X.-F. Ren and E. Turos, Tetrahedron Lett., 34, 1575 (1993).

252.

T. Kitamara, S. Soda, H. Kawasato and H. Taniguchi, Tetrahedron, 49, 5055 (1993).

253.

X. Huang, R. J. Batchelor, F. W. B. Einstein and A. J. Bennet, J. Org. Chem., 59, 7108 (1994).

254.

G. I. Borodkin, E. I. Chernyak, M. M. Shakirov and V. G. Shubin, Metalloorg. Khim., 3, 1017

 

(1990); Chem. Abstr., 114, 100774 (1991).

 

255.

E. V. Skorobogatova, E. Yu. Grudzinskaya, P. S. Afanas’ev, V. R. Kartashov, N. S. Zefirov and

 

R. Caple, Zh. Org. Khim., 23, 2052 (1987).

 

256.

Ya. D. Samuilov, V. I. Gainullin, S. E. Solov’eva and A. I. Konovalov, Zh. Org. Khim., 24, 795

 

(1988); Chem. Abstr., 109, 189586 (1988).

 

257.

Ya. D. Samuilov, V. I. Gainullin, S. E. Solov’eva and A. I. Konovalov, Dokl. Akad. Nauk SSSR,

 

317, 382 (1991); Chem. Abstr., 115, 207246 (1991).

 

258.

Ya. D. Samuilov, V. I. Gainullin, A. I. Movchan and A. I. Konovalov, Zh. Obshch. Khim., 59,

 

905 (1989); Chem. Abstr., 111, 152951 (1989).

 

259.

L. Engman, J. Org. Chem., 54, 884 (1989).

 

260.

R. Ceccherelli, M. Curini, M. C. Marcotullio and O. Rosati, Tetrahedron, 47, 4211 (1991).

261.

M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli and D. Bartoli, Tetrahedron, 44, 2261 (1988).

262.

(a) M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli and D. Bartoli, Tetrahedron, 44, 2273

 

(1988).

 

 

(b) N. Kamigata, T. Satoh and B. Yoshida, Bull. Chem. Soc. Jpn., 61, 449 (1988).

263.

P.-A. Carrupt and P. Vogel, Helv. Chim. Acta, 72, 1008 (1989).

264.

O. Arjona, R. Fernandez de la Pradilla, J. Plumet and A. Viso, Tetrahedron, 45, 4565 (1989).

265.

O. Arjona, R. Fernandez´ de la Pradilla, I. Rita-Romero, J. Plumet and A. Viso, Tetrahedron, 46,

 

8199 (1990).

 

266.

G. A. Nishevich, V. I. Mamatyuk, V. A. Barkhash,

T. N. Velikokhatikov, N. K. Sadovaya,

 

N. S. Zefirov, O. I. Lyubinskaya, G. S. Mikaelyan and V. A. Smit, Zh. Org. Khim., 26, 84

 

(1990); Chem. Abstr., 113, 114421 (1990).

 

267.

G. Haufe, G. Alvernhe, D. Anker, A. Laurent and C. Saluzzo, J. Org. Chem., 57, 714 (1992).

19. Electrophilic additions to double bonds

1217

268.S. A. Lermontov, S. I. Zavorin, A. N. Pushin, A. N. Chekhov, N. S. Zefirov and P. J. Stang,

Tetrahedron Lett., 34, 703 (1993).

269.N. S. Zefirov, N. V. Zyk, A. G. Kutateladze and E. K. Beloglazkina, Izv. Akad. Nauk SSSR, Ser. Khim., 2623 (1991); Chem. Abstr., 116, 105254 (1992).

270.L. Benati, P. C. Montevecchi and P. Spagnolo, Tetrahedron Lett., 49, 5365 (1993).

271.M. Tiecco, M. Tingoli, L. Testaferri and R. Balducci, J. Org. Chem., 57, 4025 (1992).

272.Z. K. M. Adb El Samii, M. I. Al Ashmawy and J. M. Mellor, J. Chem. Soc., Perkin Trans. 1, 2509, 2523, 2517 (1988).

273.S. Toteberg¨-Kaulen and E. Steckhan, Tetrahedron, 44, 4389 (1988).

274.M. Tiecco, L. Testaferri, M. Tingoli, D. Chianelli and D. Bartoli, Tetrahedron Lett., 30, 1417 (1989).

275.M. Tiecco, L. Testaferri, M. Tingoli and D. Bartoli, Tetrahedron, 45, 6819 (1989).

276.M. Yoshida, S. Sasage, K. Kawamura, T. Suzuki and N. Kamigata, Bull. Chem. Soc. Jpn., 64,

416 (1991).

277.A. N. Pushin, S. E. Tkachenko, I. V. Martynov, E. V. Skorobogatova, V. R. Kartashov and

N.S. Zefirov, Zh. Org. Khim., 27, 1473 (1991); Chem. Abstr., 116, 173283 (1992).

278.K. Okuma, T. Koike, S. Yamamoto, K. Yonekura and H. Ohta, Chem. Lett., 1953 (1989).

279.J. Wang, J. A. Wurster, L. J. Wilson and D. Liotta, Tetrahedron Lett., 34, 4881 (1993).

280.V. Lucchini, G. Modena and L. Pasquato, J. Chem. Soc., Chem. Commun., 1565 (1994).

281.D. L. Clive, J. Chem. Soc., Chem. Commun., 100 (1974).

282.M. Tiecco, L. Testaferri, M. Tingoli, D. Bartoli and R. Balducci, J. Org. Chem., 55, 429 (1990).

283.S. Konstantinovic,´ Z. Burgaciˇc,ˇ S. Milosavljevic,´ G. Schroth and M. L. Mihailovic,´ Justus Liebigs Ann. Chem., 261 (1992).

284.H. Inoue, S. Murata and T. Suzuki, Chem. Lett., 901 (1994).

285.R. Grigg, M. Hadjisoteriou, P. Kennewell and J. Markandu, J. Chem. Soc., Chem. Commun., 1537 (1992).

286.R. Grigg, M. Hadjisoteriou, P. Kennewell, J. Markandu and M. Thornton-Pett, J. Chem. Soc., Chem. Commun., 1388 (1992).

287.D. H. R. Barton, L. Bohe´ and X. Lusinchi, Tetrahedron Lett., 31, 93 (1990).

288.S. Fukuzawa, K. J. Irgolic and D. H. O’Brien, Organometallics, 9, 3073 (1990).

289.S. Hong and X. Fu, Huaxue Xuebao, 49, 540 (1991); Chem. Abstr., 115, 1355196 (1991).

290.R. D. Bach, A. L. Owensby, C. Gonzalez, H. B. Schlegel and J. J. W. McDouall, J. Am. Chem. Soc., 113, 2338 (1991).

291.P. Muller and J. Pfyffer, Helv. Chim. Acta, 75, 745 (1992).

292.K. J. Shea and J.-S. Kim, J. Am. Chem. Soc., 114, 3044 (1992).

293.T. Ohwada, J. Am. Chem. Soc., 114, 8818 (1992).

294.J. F. Gordon, J. R. Hanson, P. B. Hitchcock, A. G. Jarvis, H. J. Wadsworth and A. H. Ratcliffe,

J.Chem. Soc., Perkin Trans. 1, 1473 (1988).

295.P. Kocovskˇy,´ J. Chem. Soc., Perkin Trans. 1, 1759 (1994).

296.F. Fringuelli, R. Germani, F. Pizzo, F. Santinelli and G. Savelli, J. Org. Chem., 57, 1198 (1992).

297.G. Mandville, M. Ahmar and R. Bloch, Tetrahedron Lett., 34, 2119 (1993).

298.P. Kocovskˇy´ and I. Stary,´ J. Org. Chem., 55, 3236 (1990).

299.C. W. Bird and N. Hormozi, Tetrahedron Lett., 31, 3501 (1990).

300.A. A. Shered’ko, Z. G. Pikh and E. N. Mokryi, Dokl. Akad. Nauk Ukr.SSR, Ser. B, 49 (1990); Chem. Abstr., 113, 190598 (1990).

301.V. A. Anfinogenov, N. N. Malkova, E. E. Sirotina and V. D. Filimonov, Zh. Org. Khim., 25, 1482 (1989); Chem. Abstr., 112, 54684 (1990).

302.M. D. Threadgill and P. Webb, J. Chem. Soc., Chem. Commun., 269 (1991).

303.D. Hall, A.-F. Sevin and S. Warren, Tetrahedron Lett., 32, 7123 (1991).

304.M. Fujita, H. Ishizuka and K. Ogura, Tetrahedron Lett., 32, 6355 (1991).

305.O. Casher, D. O’Hagan, C. A. Rosenkranz, H. S. Rzepa and N. A. Zaidi, J. Chem. Soc., Chem. Commun., 1337 (1993).

306.R. D. Walkup and N. U. Obeyesekere, J. Org. Chem., 53, 920 (1988).

307.M. Perran, J. W. Wilt, R. Subramanian and D. S. Crumrine, J. Org. Chem., 58, 202 (1993).

308.H. Sugita, K. Mizuno, T. Saito, K. Isagawa and Y. Otsuji, Tetrahedron Lett., 33, 2539 (1992).

309.J. K. Crandall, D. M. Coppert, T. Schuster and F. Lin, J. Am. Chem. Soc., 114, 5998 (1992).

310.R. Curci, in Advances in Oxygenated Processes (Ed. A. L. Baumstark), Vol. 2, Chap. 1, JAI Press, Greenwich, CT, 1990.

1218

Pavel Kocovskˇy´

311.W. Adam and L. Hadjiarapoglou, Chem. Ber., 123, 2077 (1990).

312.R. W. Murray, D. L. Shiang and M. Singh, J. Org. Chem., 56, 3677 (1991).

313.A. L. Baumstark and P. C. Vasquez, J. Org. Chem., 53, 3437 (1988).

314.W. Adam and L. Hadjirapoglou, Top. Curr. Chem., 164, 45 (1993); Chem. Abstr., 119, 27471 (1993).

315.D. Guo, Huaxue Shji, 14, 165 (1992); Chem. Abstr., 117, 233098 (1992).

316.R. W. Murray and D. Shiang, J. Chem. Soc., Perkin Trans. 2, 349 (1990).

317.R. W. Murray and D. Gu, J. Chem. Soc., Perkin Trans. 2, 2203 (1993).

318.B. A. Marples, J. P. Muxworthy and K. H. Baggaley, Tetrahedron Lett., 32, 533 (1991).

319.A.-M. Lluch, F. Sanchez-Baeza, A. Messeguer, C. Fusco and R. Curci, Tetrahedron, 49, 6299 (1993).

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

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

322.W. Adam, E.-M. Peters, K. Peters, H. G. von Schnering and V. Voerckel, Chem. Ber., 125, 1263 (1992).

323.W. Adam, M. Ahrweiler, K. Paulini, H.-U. Reissig and V. Voerckel, Chem. Ber., 125, 2719 (1992).

324.J. K. Crandall and D. Batal, Tetrahedron Lett., 29, 4791 (1988).

325.J. K. Crandall, D. J. Batal, D. P. Sebesta and F. Lin, J. Org. Chem., 56, 1153 (1991).

326.Y. Naruta and K. Maruyama, Kikan Kagaku Sosetsu, 81 (1990); Chem. Abstr., 114, 206196 (1991).

327.Y. E. Raifel’d and A. M. Vaisman, Usp. Khim., 60, 241 (1991); Chem. Abstr., 114, 228085 (1991).

328.G. Shi, Z. Teng and X. Ding, Huaxue Tongbao, 22 (1991); Chem. Abstr., 115, 113730 (1991).

329.T. Nishiguchi and F. Asano, J. Org. Chem., 54, 1531 (1989).

330.C. J. Burns, C. A. Martin and K. B. Sharpless, J. Org. Chem., 54, 2826 (1989).

331.S. S. Woodard, M. G. Finn and K. B. Sharpless, J. Am. Chem. Soc., 113, 106 (1991).

332.M. G. Finn and K. B. Sharpless, J. Am. Chem. Soc., 113, 113 (1991).

333.E. J. Corey, J. Org. Chem., 55, 1693 (1990).

334.P. R. Carlier, W. S. Mungall, G. Schroder¨ and K. B. Sharpless, J. Am. Chem. Soc., 110, 2978 (1988).

335.B. H. McKee, T. H. Kalantar and K. B. Sharpless, J. Org. Chem., 56, 6966 (1991).

336.S. M. Brown, S. G. Davies and J. A. A. de Sousa, Tetrahedron: Asymmetry, 2, 511 (1991).

337.T. Dubuffet, C. Bidon, R. Sauvetre and J.-F. Normant, J. Organomet. Chem., 393, 173 (1990).

338.S. Takano, Y. Iwabuchi and K. Ogasawara, J. Chem. Soc., Chem. Commun., 820 (1991).

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

340.K. Yamamoto, Y. Kawanami and M. Miyazawa, J. Chem. Soc., Chem., Commun., 436 (1993).

341.T. H. Chan, L. M. Chen and D. Wang, J. Chem. Soc., Chem. Commun., 1280 (1988).

342.N. Komatsu, M. Hashizume, T. Sugita and S. Uemura, J. Org. Chem., 58, 4529 (1993).

343.N. Komatsu, Y. Nishibayashi and S. Uemura, Tetrahedron Lett., 34, 2339 (1993).

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

345.H. Pettersson, A. Gogoll and J.-E. Backvall,¨ J. Org. Chem., 57, 6025 (1992).

346.T. Hanamoto, T. Katsuki and M. Yamaguchi, Tetrahedron Lett., 28, 6191, (1987).

347.M. Bailey, I. Staton, P. R. Ashton, I. E. Marko´ and W. D. Ollis, Tetrahedron: Asymmetry, 2, 495 (1991).

348.M. Bailey, I. E. Marko´ and W. D. Ollis, Tetrahedron Lett., 32, 2687 (1991).

349.W. Adam and E. Staab, Tetrahedron Lett., 29, 531 (1988).

350.W. Adam and E. Staab, Justus Liebigs Ann. Chem., 119, 1179 (1988).

351.Y. Okamoto and W. C. Still, Tetrahedron Lett., 29, 971 (1988).

352.D. R. Gupta, Kamaluddin and S. Naithani, Proc. Indian Natl. Sci. Acad., 59A, 49 (1989); Chem. Abstr., 114, 5633 (1991).

353.L. I. Zakharkin, V. A. Likhomanenko, V. F. Tsvetkov, S. P. Korshunov, K. K. Ziganshina and V. V. Guseva, Neftekhimiya, 31, 71 (1991); Chem. Abstr., 114, 246596 (1991).

354.T. Chamberlain, X. Fu, J. T. Pechacek, X. Peng, D. M. S. Wheeler and M. M. Wheeler, Tetrahedron Lett., 32, 1707 (1991).

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

356.J. Kato, H. Ota, K. Matsukawa and T. Endo, Tetrahedron Lett., 29, 2843 (1988).

357.R. Irie, K. Noda, Y. Ito, N. Matsumoto and T. Katsuki, Tetrahedron Lett., 31, 7345 (1990).

19. Electrophilic additions to double bonds

1219

358.C. Bolm, Angew. Chem., Int. Ed. Engl., 30, 403 (1991).

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

360.D. D. Agarwal, R. P. Bhatnagar, R. Jain and S. Srivastava, J. Chem. Soc., Perkin Trans. 2, 989 (1990).

361.A. M. d’ A. R. Gonsalves, R. A. W. Johnstone, M. M. Pereira and J. Shaw, J. Chem. Soc., Perkin Trans. 1, 645 (1991).

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

363.J. P. Collman, J. I. Brauman, P. D. Hampton, H. Tanaka, D. S. Bohle and R. T. Hembre, J. Am. Chem. Soc., 112, 7980 (1990).

364.G. O. Torosyan, N. G. Oganyan, S. Banfi and F. Montanari, Metallorg. Khim., 3, 549, (1990); Chem. Abstr., 113, 171285 (1990).

365.S. Banfi, A. Maciocchi, F. Montanari and S. Quici, Gazz. Chim. Ital., 120, 123 (1990); Chem. Abstr., 113, 131342 (1990).

366.S. Banfi, A. Maciocchi, A. Moggi, F. Montanari and S. Quici, J. Chem. Soc., Chem. Commun., 1794 (1990).

367.H. Turk and W. T. Ford, J. Org. Chem., 56, 1253 (1991).

368.A. W. Van der Made, R. J. M. Nolte and W. Drenth, Recl. Trav. Chim. Pays-Bas, 109, 537 (1990); Chem. Abstr., 114, 246577 (1991).

369.S. Tang and R. M. Kennedy, Tetrahedron Lett., 33, 5299 (1992).

370.S. Tang and R. M. Kennedy, Tetrahedron Lett., 33, 5303 (1992).

371.G. Xie, L. Xu, J. Hu, S. Ma, W. Hou and F. Tao, Tetrahedron Lett., 29, 2967 (1988).

372.J. E. G. Kemp, in Comprehensive Organic Synthesis (Eds. B. M. Trost and I. Fleming), Vol. 7, Pergamon, Oxford, 1991.

373.D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc.,

(a) 115, 5328 (1993); (b) 116, 2742 (1994).

374.Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 115, 5326 (1993).

375.R. S. Atkinson, in Azides and Nitrenes (Ed. E. F. V. Scriven), Academic Press, New York, 1984.

376.R. S. Atkinson, M. J. Grimshire and B. J. Kelly, Tetrahedron, 45, 2875 (1989).

377.R. S. Atkinson, E. Barker, J. Chem. Soc., Chem. Commun., 819 (1995).

378.R. S. Atkinson, J. Fawcett, D. R. Russell and P. J. Williams, J. Chem. Soc., Chem. Commun., 2031 (1994).

379.R. S. Atkinson, J. Fawcett, D. R. Russell and P. J. Williams, Tetrahedron Lett., 36, 3241 (1995).

380.R. S. Atkinson, M. P. Coogan and I. S. T. Lochrie, J. Chem. Soc., Chem. Commun., 789 (1996).

381.C. Schade, H. Mayr and E. M. Arnett, J. Am. Chem. Soc., 110, 567 (1988).

382.M. Roth, C. Schade and H. Mayr, J. Org. Chem., 59, 169 (1994).

383.H. Mayr and G. Hagen, J. Chem. Soc., Chem. Commun., 91 (1989).

384.J.-P. Dau-Schmidt and H. Mayr, Chem. Ber., 127, 205 (1994).

385.H. Mayr and J.-P. Dau-Schmidt, Chem. Ber., 127, 213 (1994).

386.M. A. Brock, T. Sebastian, R. Jueschke and C. Dallaire, J. Org. Chem., 56, 2273 (1991).

387.E. Muks, M. Railjan, I. Loiveke and H. Mare, Eesti Tead. Akad. Toim., Keem, 41, 26 (1992);

Chem. Abstr., 120, 269322 (1994).

388. I. M. Brudnik, D. V. Shornikov, I. G. Bresler, R. T. Akhmatdinov, E. A. Kantor and

D. L. Rakhmankulov, Zh. Org. Khim., 25, 814 (1989); Chem. Abstr., 112, 97963 (1990).

389.A. Ketter and R. Herrmann, J. Organomet. Chem., 386, 241 (1990).

390.T. Mukaiyama, K. Wariishi, Y. Saito, M. Hayashi and S. Kobayashi, Chem. Lett., 1101 (1988).

391.Y. Li and K. N. Houk, J. Am. Chem. Soc., 111, 1236 (1989).

392.H. Waldmann, G. Schmidt, M. Jansen and J. Geb, Tetrahedron Lett., 34, 5867 (1993).

393.Y. Ukai, K. Tsukamoto, Y. Nasada, M. Shimizu and T. Fujisawa, Chem. Lett., 221 (1993).

394.I. I. Ibragimov, E. I. Mamedov, A. T. Ismailov, A. G. Aliev, Sh. Z. I. Mekhtieva, V. G. Dzhafarov and V. I. Belyaeva, Zh. Org. Khim., 26, 1648 (1990); Chem. Abstr., 114, 142254 (1991).

395.M. Hojo, R. Masuda, Y. Kamitori and E. Okada, J. Org. Chem., 56, 1975 (1991).

396.C. E. Harding and G. R. Stanford, J. Org. Chem., 54, 3055 (1989).

397.W. Fan and J. B. White, Tetrahedron Lett., 34, 957 (1993).

398.K. H. Schulte-Elte, H. Pamingle, A. P. Uijttewaal and R. L. Snowden, Helv. Chim. Acta, 75, 759 (1992).

399.R. L. Snowden, J.-C. Eichenberger, S. M. Linder, P. Sonnay, C. Vial and K. H. Schulte-Elte J. Org. Chem., 57, 955 (1992).

400.Lj. Dosenˇ-Micovi´c,´ Lj. Lorenc and M. L. Mihailovic,´ Tetrahedron, 46, 3659 (1990).

1220

Pavel Kocovskˇy´

401.R. M. Schonk, B. H. Bakker and H. Cerfontain, Recl. Trav. Chim. Pays-Bas, 111, 389 (1992); Chem Abstr., 118, 59100 (1993).

402.M. Peeran, J. W. Wilt, R. Subramanian and D. S. Crumrine, J. Org. Chem., 58, 202 (1993).

403.S. K. Taylor, S. A. May and J. A. Hopkins, Tetrahedron Lett., 34, 1283 (1993).

404.W. S. Johnson, D. Guay and U. Schubert, J. Org. Chem., 54, 4731 (1989).

405.(a) W. S. Johnson, B. Chenera, F. S. Tham and R. K. Kullnig, J. Am. Chem. Soc., 115, 493, (1993).

(b)W. S. Johnson, V. R. Fletcher, B. Chenera, W. R. Bartlett, F. S. Tham and R. K. Kullnig, J. Am. Chem. Soc., 115, 497 (1993).

(c)W. S. Johnson, R. A. Buchanan, W. R. Bartlett, F. S. Tham and R. K. Kullnig, J. Am. Chem. Soc., 115, 504 (1993).

(d)W. S. Johnson, M. S. Plummer, S. P. Reddy and W. R. Bartlett, J. Am. Chem. Soc., 115, 515 (1993).

406.P. V. Fish and W. S. Johnson, J. Org. Chem., 59, 2324 (1994).

407.P. V. Fish, W. S. Johnson, G. S. Jones, F. S. Tham and R. K. Kulling, J. Org. Chem., 59, 6150 (1994).

408.P. V. Fish and W. S. Johnson, Tetrahedron Lett., 35, 1469 (1994).

409.P. V. Fish, A. R. Sudhakar and W. S. Johnson, Tetrahedron Lett., 34, 7849 (1993).

410.W. S. Johnson, Tetrahedron, 47, No. 41, pp. xi l (1991), Tetrahedron Prize.

411.D. J. Nelson and R. Soundararajan, Tetrahedron Lett., 29, 6207 (1988).

412.M. Kimura, K. Fugami, S. Tanaka and Y. Tamaru, Tetrahedron Lett., 32, 6359 (1991).

413.D. N. A. Fox and T. Gallagher, Tetrahedron, 46, 4697 (1990).

414.I. W. Davies, T. Gallagher, R. B. Lamont and D. I. C. Scopes, J. Chem. Soc., Chem. Commun., 335 (1992).

415.H. B. Broughton, S. M. Green and H. S. Rzepa, J. Chem. Soc., Chem. Commun., 998 (1992).

416.A. S. Cieplak, B. D. Tait and C. R. Johnson, J. Am. Chem. Soc., 111, 8447 (1989).

417.J. Barluenga, J. Perez-Prieto and G. Asensio, Tetrahedron, 46, 2453 (1990).

418.J. M. Takacs, M. A. Helle, B. J. Sanyal and T. A. Eberspracher, Tetrahedron Lett., 31, 6765 (1990).

419.J. Barluenga, F. Aznar, S. Fraiz and A. C. Pinto, Tetrahedron Lett., 32, 3205 (1991).

420.P. Kocovskˇy,´ Organometallics, 12, 1969 (1993).

421.R. D. Walkup and G. Park, J. Am. Chem. Soc., 112, 1597 (1990).

422.J.-R. Pougny, M. A. M. Nassr and P. Sinay, J. Chem. Soc., Chem. Commun., 375 (1981).

423.M. A. Tius and J. Busch-Petersen, Tetrahedron Lett., 35, 5181 (1994).

424.N. Gnonlonfoun, Bull. Soc. Chim. Fr. II, 862 (1988).

425.A. J. Bloodworth, R. J. Curtis and N. Mistry, J. Chem. Soc., Chem. Commun., 954 (1989).

426.P. Welzel, W. Holtmeier and B. Wessling, Justus Liebigs Ann. Chem., 1327 (1978).

427.P. Kocovskˇy´ and R. S. Baines, Tetrahedron Lett., 34, 6139 (1993).

428.P. Kocovskˇy´ and R. S. Baines, J. Org. Chem., 59, 5439 (1994).

429.M. L. Mihailovic,´ R. Vukicevi´c,´ S. Konstantinovic,´ S. Milosavljevic´ and G. Schroth, Justus Liebigs Ann. Chem., 305 (1992).

430.J. P. Michael, P. C. Ting and P. A. Bartlett, J. Org. Chem., 50, 2416 (1985).

431.P. Kocovskˇy,´ V. Langer and A. Gogoll, J. Chem. Soc., Chem. Commun., 1026 (1990).

432.R. M. Sharma, E. D. Martinez and H. Zolfaghari, J. Chem. Res. (S), 237 (1990).

433.Yu. A. Serguchev and R. B. Gustulyak, Zh. Org. Khim., 26, 2066 (1991); Chem. Abstr., 115, 158144 (1991).

434.T. Ando, P. Bauchat, A. Foucaud, M. Fujita, T. Kimura and H. Sohmiya, Tetrahedron Lett., 32, 6379 (1991).

435.(a) M. F. Semmelhack, W. R. Epa, A. Cheung, Y. Gu, C. Kim, N. Zhang and W. Lew, J. Am. Chem. Soc., 116, 7455 (1994).

For an overview, see:

(b)M. F. Semmelhack, C. Kim, N. Zhang, C. Bodurow, M. Sanner, W. Dobler and M. Meier,

Pure Appl. Chem., 62, 2035 (1990).

436.R. A. T. M. van Bethem, H. Hiemstra and W. N. Speckamp, J. Org. Chem., 57, 6083 (1992).

437.R. C. Larock and T. R. Hightower, J. Org. Chem., 58, 5298 (1993).

438.M. Ronn,¨ J.-E. Backvall¨ and P. G. Andersson, Tetrahedron Lett., 36, 7749 (1995).

439.Y. Tamaru, H. Tanigawa, S. Itoh, M. Kimura, S. Tanaka, K. Fugami, T. Sekiyama and Z. Yoshida,

Tetrahedron Lett., 33, 631 (1992).

19. Electrophilic additions to double bonds

1221

440.M. Kimura, K. Fugami, S. Tanaka and Y. Tamaru, J. Org. Chem., 57, 6376 (1992).

441.M. Kimura, H. Harayama, S. Tanaka and Y. Tamaru, J. Chem. Soc., Chem. Commun., 2531 (1994).

442.D. Bouyssi, G. Balme, G. Fournet, N. Monteneiro and J. Gore, Tetrahedron Lett., 32, 1641 (1991).

443.N. Monteneiro, G. Balme and J. Gore, Tetrahedron Lett., 32, 1645 (1991).

444.Yu. G. Noskov, M. I. Terekhova and E. S. Petrov, Kinet. Katal., 30, 234 (1989); Chem. Abstr., 112, 157576 (1990).

445.M. Hodgson, D. Parker, R. J. Taylor and G. Ferguson, Organometallics, 7, 176 (1988).

446.Y. Uozumi and T. Hayashi, J. Am. Chem. Soc., 113, 9887 (1991).

447.M. Murakami, P. G. Andersson, M. Suginome and Y. Ito, J. Am. Chem. Soc., 113, 3987 (1991).

448.A. de Meijer and F. E. Meyer, Angew. Chem., Int. Ed. Engl., 33, 2379 (1994).

449.W. Cabri and I. Candiani, Acc. Chem. Res., 28, 2 (1995).

450.C. Amatore, A. Jutand and M. A. M’Barki, Organometallics, 11, 3009 (1992).

451.R. Grigg, P. Kennewell and A. S. Teasdale, Tetrahedron Lett., 33, 7785 (1992).

452.R. C. Larock and D. E. Stinn, Tetrahedron Lett., 30, 2767 (1989).

453.G. D. Harris, R. J. Herr and S. M. Weinreb, J. Org. Chem., 57, 2528 (1992).

454.R. Benharddou, S. Chernecki and G. Ville, J. Chem. Soc., Chem. Commun., 247 (1988).

455.R. Grigg, P. Stevenson and T. Worakun, Tetrahedron, 44, 2033 (1988).

456.R. Grigg, P. Stevenson and T. Worakun, Tetrahedron, 44, 2049 (1988).

457.K. Ikenaga, S. Matsumoto, K. Kikukawa and T. Matsuda, Chem. Lett., 873 (1988).

458.S. Ganguly and D. M. Roundhill, J. Chem. Soc., Chem. Commun., 639 (1991).

459.T. Hosokawa, T. Shinohara, Y. Ooka and S. Murahashi, Chem. Lett., 2001 (1989).

460.Y. Yamamoto, M. Al-Masun and N. Asao, J. Am. Chem. Soc., 116, 6019 (1994).

461.J.-E. Backvall¨ and P. G. Andersson, J. Am. Chem. Soc., 112, 3683 (1990).

462.J.-E. Backvall¨ and P. G. Andersson, J. Am. Chem. Soc., 114, 6374 (1992).

463.J.-E. Backvall¨ and P. G. Andersson, J. Org. Chem., 56, 2274 (1991).

464.P. G. Andersson, Y. I. M. Nilsson and J.-E. Backvall,¨ Tetrahedron, 50, 559 (1994).

465.J.-E. Backvall,¨ Acc. Chem. Res., 16, 335 (1983).

466.J.-E. Backvall,¨ New J. Chem., 14, 447 (1990).

467.P. G. Andersson and J.-E. Backvall,¨ J. Am. Chem. Soc., 114, 8696 (1992).

468.R. C. Larock, Y. Lu, A. C. Bain and C. E. Russell, J. Org. Chem., 56, 4589 (1991).

469.B. M. Trost and Y. Shi, J. Am. Chem. Soc., 113, 701 (1991).

470.I. Ojima, K. Kato, M. Okabe and T. Fuchikami, J. Am. Chem. Soc., 109, 7714 (1987).

471.A. M. Trzeciak and J. J. Ziolkowski, J. Mol. Catal., 43, 335 (1988); Chem. Abstr., 109, 72777 (1988).

472.A. R. El’man, V. I. Kurkin, E. V. Slivinskii and S. M. Loktev, Neftekhimia, 30, 46 (1990); Chem. Abstr., 112, 197383 (1990).

473.T. V. RajanBabu and A. L. Casalnuovo, J. Am. Chem. Soc., 114, 6265 (1992).

474.S. H. Bergens, P. Noheda, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 114, 2121 (1992).

475.S. H. Bergens, P. Noheda, J. Whelan and B. Bosnich, J. Am. Chem. Soc., 114, 2128 (1992).

476.R. W. Barnhart, X. Wang, P. Noheda, S. H. Bergens, J. Wheland and B. Bosnich, Tetrahedron 50, 4335 (1994).

477. E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan and

J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994).

478.H. C. Kolb, P. G. Andersson, Y. L. Bennani, G. A. Crispino, K.-S. Jeong, H.-L. Kwong and

K. B. Sharpless, J. Am. Chem. Soc., 115, 12226 (1993).

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

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

481.(a) H. C. Kolb, M. S. Van Nieuwen and K. B. Sharpless, Chem. Rev., 94, 2487 (1994).

(b) D. J. Berrisford, C. Bolm and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 34, 1059 (1995).

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

483.E. J. Corey and M. C. Noe, J. Am. Chem. Soc., 115, 12579 (1993).

484.R. L. Halterman and M. A. Evoy, J. Am. Chem. Soc., 114, 980 (1992).

485.D. J. Krysan, T. W. Rockaway and A. R. Haight, Tetrahedron Asymmetry, 5, 625 (1994).

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

487. For an earlier, stoichiometric, non-asymmetric work, see: A. O. Chong, K. Oshima and K. B. Sharpless, J. Am. Chem. Soc., 99, 3420 (1977).

1222

Pavel Kocovskˇy´

488.M.-H. Cheng, Y.-H. Ho, G.-H. Lee, S.-M. Peng and R. S. Liu, J. Chem. Soc., Chem. Commun., 697 (1991).

489.A. J. Pearson and V. D. Khetani, J. Am. Chem. Soc., 111, 6778 (1989).

490.I. Marko´ and P. F. Richardson, Tetrahedron Lett., 32, 1831 (1991).

491.F. Bellesia, F. Ghelfi, V. M. Pagnoni and A. Pinetti, J. Chem. Res. (S), 108 (1989).

492.M. S. Symala, J. Das, S. Baskaran and S. Chandrasekaran, J. Org. Chem., 57, 1928 (1992).

493.R. M. Kennedy and S. Tang, Tetrahedron Lett., 33, 3729 (1992).

494.Y. Yang, F. Diederich and J. S. Valentine, J. Am. Chem. Soc., 113, 7195 (1991).

495.J. A. S. Howell, M.-C. Tirvengadum and G. Walton, J. Organomet. Chem., 338, 217 (1988).

496.M. Brookhardt and B. E. Grant, J. Am. Chem. Soc., 115, 2151 (1993).

497.I. E. Kingma, M. Wiersma, J. L. van der Baan, S. Balt, F. Bickelhaupt, M. W. G. De Boaster, G. W. Klumpp and A. L. Spek, J. Chem. Soc., Chem. Commun., 832 (1993).

498.A. L. Casalnuovo, J. C. Calabrese and D. Milstein J. Am. Chem. Soc., 110, 6738 (1988).

499.D. Steinborn and R. Taube, Proc. Conf. Coord. Chem., 11th, 383 (1987); Chem. Abstr., 109, 92043 (1988).

500.K. Tamao, Y. Nakagawa, Y. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 110, 3712 (1988).

501.L. N. Lewis, K. G. Sy and P. E. Donajue, J. Organomet. Chem., 427, 165 (1992).

502.M. R. Gagne,´ C. L. Stern and T. J. Marks, J. Am. Chem. Soc., 114, 275 (1992).

503.G. A. Molander and J. O. Hoberg, J. Am. Chem. Soc., 114, 3123 (1992).

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