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.
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页码：4 / 5
页数：2
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