ASYMMETRIC-SYNTHESIS OF (2S,3S)-PROLINOMETHIONINES AND (2S,3R)-3-PROLINOMETHIONINES - 3-METHYLSULFANYLMETHYL-PYRROLIDINE-2-CARBOXYLIC ACIDS

Authors
KAROYAN P CHASSAING G
Citation
P. Karoyan et G. Chassaing, ASYMMETRIC-SYNTHESIS OF (2S,3S)-PROLINOMETHIONINES AND (2S,3R)-3-PROLINOMETHIONINES - 3-METHYLSULFANYLMETHYL-PYRROLIDINE-2-CARBOXYLIC ACIDS, Tetrahedron : asymmetry, 8(12), 1997, pp. 2025-2032
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
12
Year of publication
1997
Pages
2025 - 2032
Database
ISI
SICI code
0957-4166(1997)8:12<2025:AO(A(>2.0.ZU;2-T
Abstract
The synthesis of 3-prolinomethionine can be easily achieved in a diast ereoselective and enantioselective way via zinc-enolate cyclisation. A fter transmetallation by CuCN.2LiCl, the zinc-copper derivative was re acted with S-methyl methanesulfonothioate leading in a ''one-pot'' pro cedure, to N-(alpha-methylbenzyl)-3-prolinomethionine benzyl ester. Th e alpha-methylbenzyl group was transformed in vinyl-oxycarbonyl and te rtiobutyloxycarbonyl groups successively. Reprotonation of cis Voc pro linomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer. (C) 1997 Elsevier Science Ltd.