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.
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页码：10879 / 10888
页数：10
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