Highly enantioselective decarboxylative protonation of α-aminomalonates mediated by thiourea Cinchona alkaloid derivatives:: Access to both enantiomers of cyclic and acyclic α-aminoacids

被引:88
作者
Amere, Mukkanti [1 ]
Lasne, Marie-Claire [1 ]
Rouden, Jacques [1 ]
机构
[1] Univ Caen Basse Normandie, ENSICAEN, CNRS, Lab Chim Mol & Thioorgan, F-14050 Caen, France
关键词
D O I
10.1021/ol070712v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiourea derived cinchona alkaloids promote the asymmetric decarboxylative protonation of cyclic, acyclic, or bicyclic alpha-aminomalonate hemiesters under mild and metal-free conditions to afford enantioenriched aminoesters in high yields and enantioselectivities up to 93%. Both enantiomers of the aminoesters have been synthesized with the same selectivity when using organic base 3 and its pseudoenantiomer 6 derived from quinine.
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页码:2621 / 2624
页数:4
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