A simple, stereoselective synthesis of ketomethylene dipeptide isosteres

被引:27
作者
Hoffman, RV
Tao, JH
机构
[1] Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces
关键词
D O I
10.1016/S0040-4020(97)00410-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-gamma-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7119 / 7126
页数:8
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