STEREOSELECTIVE RADICAL ADDITIONS OF GAMMA-OXY-ALPHA,BETA-UNSATURATED ESTER DERIVATIVES - 1,2-ASYMMETRIC INDUCTION IN ACYCLIC AND CYCLIZATION SYSTEMS

被引：18

作者：

MORIKAWA, T

WASHIO, Y

HARADA, S

HANAI, R

KAYASHITA, T

NEMOTO, H

SHIRO, M

TAGUCHI, T

机构：

[1] TOKYO COLL PHARM,HACHIOJI 19203,TOKYO,JAPAN

[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 03期

关键词：

D O I：

10.1039/p19950000271

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Examination was made of 1,2-asymmetric induction in the addition of alkyl radicals to gamma-oxy-alpha,beta-unsaturated ester derivatives 1 and 2 prepared from ethyl lactate and (R)-2,3-0-isopropylideneglyceraldehyde 3, respectively. The addition reactions of hexyl, cyclohexyl and 3-phenylpropyl radicals to (Z)-2 derived from aldehyde 3 gave beta-addition products with syn-stereoselectivity (syn:anti = 8.6:1-syn only). The reactions of (E)-2 were non-stereoselective. Based on allylic strain, a transition-state model for the syn-stereoselectivity is proposed. 1,2-Asymmetric induction was carried out in radical cyclisation to synthesize optically active cyclohexane derivatives.

引用

页码：271 / 281

页数：11

共 38 条

[31] NEW CHIRAL AUXILIARY FOR ASYMMETRIC THERMAL-REACTIONS - HIGH REGIOSELECTIVITY AND BETA-STEREOSELECTIVITY IN ASYMMETRIC RADICAL-ADDITION REACTIONS TO MIXED FUMARIMIDES [J].