HIGH DIASTEREOFACIAL SELECTIVITY IN THE CONJUGATE ADDITION OF PHENYLMAGNESIUM BROMIDE TO ACYCLIC ALPHA-ENONES WITH AN ASYMMETRIC CARBON AT THE GAMMA-POSITION

被引：2

作者：

IBARRA, CA ^{[1
]}

PEREZ, MSA ^{[1
]}

DECASTRO, I ^{[1
]}

FERNANDEZ, MJ ^{[1
]}

机构：

[1] UNIV ALCALA DE HENARES,DEPT QUIM ORGAN,E-28871 ALCALA DE HENARES,SPAIN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1991年 / 04期

关键词：

D O I：

10.1039/p29910000467

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Moderately high diastereofacial preference has been observed in the conjugate addition of phenylmagesium bromide to the acyclic alpha-enones with an asymmetric carbon at the gamma-position (4E,6RS)-2,2,7,7-tetramethyl-6-phenyloct-4-en-3-one (1), (2E,4RS)-5,5-dimethyl-1,4-diphenylhex-2-en-1-one (2), and (4E,6RS)-2,2-dimethyl-6-phenylhept-4-en-3-one (3). The RR,SS selectivity is practically unaffected by the addition of copper(1) salts. These results are in qualitative agreement with the selectivity predicted by a Felkin-like transition state model. The method is shown to be useful for the stereoselective preparation of acyclic ketones having two chiral centres.

引用

页码：467 / 470

页数：4

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