ENANTIOSELECTIVE SYNTHESIS OF DIVERSE ALPHA-AMINO PHOSPHONATE DIESTERS

被引：182

作者：

SMITH, AB ^{[1
]}

YAGER, KM ^{[1
]}

TAYLOR, CM ^{[1
]}

机构：

[1] UNIV PENN,DEPT CHEM,MONELL CHEM SENSES CTR,PHILADELPHIA,PA 19104

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 44期

关键词：

D O I：

10.1021/ja00149a011

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient, versatile protocol for the synthesis of highly enantioenriched alpha-amino phosphonate diesters has been devised. Addition of lithium diethyl phosphite to chiral chelating imines 31a-j, prepared from a variety of aldehydes and the chiral auxiliary (R)-(-)-1-amino-1-phenyl-2-methoxyethane (29), generated predominantly the (R,R) diastereomers 33. Hydrogenolysis then furnished alpha-amino phosphonates 15; in most examples, the enantiomeric purity exceeded 97% ee.

引用

页码：10879 / 10888

页数：10