ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA CHIRAL N-ALKYLIDENESULFINAMIDES

被引:61
作者
HUA, DH
LAGNEAU, N
WANG, H
CHEN, JS
机构
[1] Department of Chemistry, Kansas State University, Manhattan
关键词
D O I
10.1016/0957-4166(95)00010-M
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(SR)-(-)-N-[1-(Triethoxymethyl)ethylidene]-p-toluenesulfinamide (2) was synthesized from the addition reaction of triethoxyacetonitrile with MeLi followed by (+)-(R)-d-menthyl p-toluenesulfinate (1R). Sulfinimine 2 underwent complete stereoselective reduction with 9-BBN and addition reaction with allylmagnesium bromide. Optically pure alpha-amino acids were synthesized from these adducts by simple hydrolysis.
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页码:349 / 352
页数:4
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