A HIGHLY ENANTIOSELECTIVE SYNTHESIS OF PHOSPHATE TRIESTERS

被引:28
作者
NAKAYAMA, K [1 ]
THOMPSON, WJ [1 ]
机构
[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024
关键词
D O I
10.1021/ja00175a030
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general methodology for the preparation of both enantiomers of a variety of trialkyl phosphates with enantiomeric excesses ranging from 87 to 92% is described. Bis(2,4-dichlorophenyl) phosphoramidates bearing a 2-substituted pyrrolidine moiety as the chiral auxiliary are prepared and examined for their stereoselectivity. Considerations based on both the absolute configuration of the product phosphates as well as the X-ray structural determination of one of the bis(2,4-dichlorophenyl) phosphoramidates suggest these substitutions occur with preponderant inversion of configuration at phosphorus. © 1990, American Chemical Society. All rights reserved.
引用
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页码:6936 / 6942
页数:7
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