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Highly enantioselective decarboxylative protonation of alpha-aminomalonates mediated by thiourea cinchona alkaloid derivatives: access to both enantiomers of cyclic and acyclic alpha-aminoacids.

Authors :
Amere M
Lasne MC
Rouden J
Source :
Organic letters [Org Lett] 2007 Jul 05; Vol. 9 (14), pp. 2621-4. Date of Electronic Publication: 2007 Jun 19.
Publication Year :
2007

Abstract

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.

Details

Language :
English
ISSN :
1523-7060
Volume :
9
Issue :
14
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
17579443
Full Text :
https://doi.org/10.1021/ol070712v