STEREOSPECIFIC NUCLEOPHILIC-ADDITION REACTIONS TO OLEFINS - ADDITION OF THIOLS TO ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID DERIVATIVES

被引：80

作者：

MIYATA, O

SHINADA, T

NINOMIYA, I

NAITO, T

DATE, T

OKAMURA, K

INAGAKI, S

机构：

[1] KOBE WOMENS COLL PHARM,KOBE 658,JAPAN

[2] TANABE SEIYAKU CO LTD,ORGAN CHEM RES LAB,TODA,SAITAMA 335,JAPAN

[3] GIFU UNIV,FAC ENGN,DEPT CHEM,GIFU 50111,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 23期

关键词：

D O I：

10.1021/jo00023a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-unsaturated carboxylic acids is described. The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source. Erythro and threo adducts are obtained with high diasteroselectivity from E and Z olefins, respectively. This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.

引用

页码：6556 / 6564

页数：9

共 36 条

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