Stereospecific construction of chiral quaternary carbon compounds from chiral secondary alcohol derivatives

被引：33

作者：

Masaki, Y ^{[1
]}

Arasaki, H ^{[1
]}

Iwata, M ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan

来源：

CHEMISTRY LETTERS | 2003年 / 32卷 / 01期

关键词：

D O I：

10.1246/cl.2003.4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral tertiary dichloromethylcarbinol derivatives, prepared by stereospecific alpha C-H insertion reaction of dichlorocarbene with protected chiral secondary alcohols, were converted into intermediary alpha-chloroepoxides which gave stereospecifically chiral quaternary carbon compounds, alpha-aminoacids via alpha-azide-aldehydes and alpha-cyanoacetic acids through cyanation, respectively. The fashion generating the quaternary centers from dichloromethylcarbinols via alpha-chloroepoxides was proved to be quite different depending on the substrates: inversion of configuration of non-benzylic substrates and apparent retention with benzylic one.

引用

页码：4 / 5

页数：2

共 47 条

[1] CHEMICAL AND BIOLOGICAL SYNTHESIS OF CHIRAL EPOXIDES [J].