(2,3) WITTIG REARRANGEMENT OF BENZYLTRICARBONYLCHROMIUM ALLYL OR CROTYL ETHERS

被引：3

作者：

MAHMOUDI, M ^{[1
]}

PELINSKI, L ^{[1
]}

MACIEJEWSKI, L ^{[1
]}

BROCARD, J ^{[1
]}

机构：

[1] UNIV SCI & TECH LILLE FLANDRES ARTOIS,SYNTH ORGAN LAB,F-59655 VILLENEUVE DASCQ,FRANCE

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1991年 / 405卷 / 01期

关键词：

D O I：

10.1016/0022-328X(91)83159-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The (2,3) Wittig rearrangement of ortho-substituted benzyl tricarbonyl chromium allyl ether occurs with complete stereoselectivity. The ortho-substituted benzyl tricarbonyl chromium E crotyl ether gives exclusively erythro diastereoisomer, the Z isomer gives a mixture (ratio 59/41) of threo and erythro diastereoisomers.

引用

页码：93 / 99

页数：7

共 16 条

[1] STEREOSPECIFIC CONVERSION OF N,N-DIMETHYLAMPHETAMINE INTO N-METHYL-PSEUDOEPHEDRINE [J].

BLAGG, J ;

DAVIES, SG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (10) :653-654

[2] ELABORATION OF ALPHA-SUBSTITUTED BENZYL ALKYL ETHERS AND SULFIDES BY SUPPRESSION OF THE WITTIG AND RELATED REARRANGEMENTS VIA COMPLEXATION TO TRICARBONYLCHROMIUM [J].

BLAGG, J ;

DAVIES, SG ;

HOLMAN, NJ ;

LAUGHTON, CA ;

MOBBS, BE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09) :1581-1589

[3] INDUCTION OF A BENZYL CHIRAL CENTER BY FORMATION OF A METALLOCENE CHIRAL CENTER - COMPLEXING OF BENZYLIC ALCOHOLS VIA HEXACARBONYL CHROMIUM [J].

BROCARD, J ;

PELINSKI, L ;

LEBIBI, J ;

MAHMOUDI, M ;

MACIEJEWSKI, L .

TETRAHEDRON, 1989, 45 (03) :709-720

[4] DIASTEREOSELECTIVE REACTION OF CARBANIONS ISSUED FROM TRICARBONYL CHROMIUM ARENES [J].

BROCARD, J ;

LEBIBI, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 310 (03) :C63-C65

[5] DIASTEREOSPECIFIC (2,3) - WITTIG-REARRANGEMENT IN CHROME TRICARBONYL ALLYL ETHERS [J].

BROCARD, J ;

MAHMOUDI, M ;

PELINSKI, L ;

MACIEJEWSKI, L .

TETRAHEDRON LETTERS, 1989, 30 (19) :2549-2552

[6] CHROMIUM(II) MEDIATED THREO SELECTIVE SYNTHESIS OF HOMOALLYL ALCOHOLS [J].

HIYAMA, T ;

KIMURA, K ;

NOZAKI, H .

TETRAHEDRON LETTERS, 1981, 22 (11) :1037-1040

[7]

Mahaffy C. A. L., 1979, INORG SYNTH, V19, P154

[8] ASYMMETRIC [2,3]WITTIG SIGMATROPIC REARRANGEMENT INVOLVING A CHIRAL AZAENOLATE AS THE MIGRATING TERMINUS - A SIMPLE SYNTHESIS OF (+)-VERRUCARINOLACTONE [J].

MIKAMI, K ;

FUJIMOTO, K ;

KASUGA, T ;

NAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (52) :6011-6014

[9]

MIKAMI K, 1983, J ORG CHEM, V48, P281

[10] [2,3]-WITTIG SIGMATROPIC REARRANGEMENTS IN ORGANIC-SYNTHESIS [J].

NAKAI, T ;

MIKAMI, K .

CHEMICAL REVIEWS, 1986, 86 (05) :885-902

← 1 2 →