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Казанский национальный исследовательский технологический университет

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Химия

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Organic Reaction Mechanisms 1997

.pdf

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J #

! "

K K

! " $ &

% $ &

			CHO
			+
O				N
				N
		O		–
				–

	(70)

SiMe3

O	OH
O

O N

C6H5Me

heat

(71)

(72)

+ 63%

(73)

SCHEME 25

Ac2O, ∆

SiMe3

O–

N+

(74)

–CO2

(75) 51%

SCHEME 26

		O
Ph2Si	O			hν (3000 Å)
Ph2Si		O	NMe MeCN, isoprene
	O
	O
		N	O
		N
		Ph
		Ph
	(76)

Ph2Si	O		NMe
	O
		N
			O
	Ph		O
	Ph
	(78)

		O
EtO2C				CO2Me
EtO2C		N		CO2Me



Me			N2
Me	N O

	Me

hν (2537 Å) quartz, MeCN

SCHEME 27

Rh2(OAc)4

heat

SCHEME 28

	O			O	O
Ph2Si					O
Ph2Si		O
O		O
O
			N	O	NMe
			N		NMe
		Ph
		Ph
(77)		73%, ds = 12 : 1
				Me
		O		N
		O
H		N
Ph		O
Ph		O		Si
		O		Si

Ph2

(79) 71%, ds = 10 : 1

				O–

EtO2C			N+
EtO2C


	Me	N O		CO2Me

		Me
		(80)

EtO2C					O
EtO2C			N
Me			N	O	CO2Me
		N
		N

		Me
	(81)			88%

O–

PhH

hν

heat

PhH

acetone

(83)

14%

(84) 76%

(82)

SCHEME 29

NO2

MeBnN

MeBnN S

O2N

+ Ar

–

CH2Cl2, 0 °C

Ph NO2

(85)

(86)

(87)

O2N

CONHR

MeBnN

CONHR

MeBnN

(88)

(89)

SCHEME 30

M $

M ! " M

K M

! "

M #

K #

						SAr
O O				O				O	OTBS
									Me
									Me
O			TBSOTf, Et3N O			OTBS	C6H5Me, heat
	Me	SAr			Me			O	SAr
	Me				Me


									H
	CO2Me				CO2Me				CO2Me
									CO2Me

			(90)			46%			(91) >95% cis

SCHEME 31


	OTr
Me	O			Me			OH	Me	OH
	1. DMA, DTBH,			Me			OH	Me	OH
	1. DMA, DTBH,
Me			250 °C			O	+		O
Me	2. aq. HCl						+
	2. aq. HCl
				H				H
	(92)			Me				Me
	(92)			1			:	3
				1			:	3
	Me
	OBn
Me	OBn				Me		OBn	Me	OBn
Me	OBn				Me			Me
		DMA, DTBH				OBn +			OBn

Me			250 °C

				H				H
				H				H
				Me				Me
	(93)			3			:	1

SCHEME 32

	O				O	X
TBSO					O	X
TBSO		N				H
O		N			TBSO	H
					TBSO
				CH2Cl2
	O
				rt, 24 h		H
				rt, 24 h

			(95) 81%
			(95) 81%
(94)



					O	Me
					N	H
					N
						H


					(96) (–)-isopulo’upone
				SCHEME 33


Ph		Ph		Ph
		Ph		Ph
	5 mol% Pd(PP3)4		H	H
C			Pd

	THF, rt, 2 d			Pd
Me3Si	THF, rt, 2 d
Me3Si			SiMe3
(97)			SiMe3	SiMe3
(97)

SiMe3

(98) 90%

SCHEME 34

# #

MeO W(CO)5

Ph MeO –

W(CO)5

THF

OMe

20 °C, 5–360 min

(99)

(100)

(101)

(102)

SCHEME 35

K K J

M M

MeCN

(103)	(104)	(105)
	SCHEME 36

M J

M M

NC N

110 °C, 26 h

NC N

73%

3 : 2

(106)

SCHEME 37

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