4-BENZYL-2,3-DIDEHYDROPROLINATE AS A HOMOCHIRAL TEMPLATE FOR MICHAEL ADDITIONS - SYNTHESIS OF ENANTIOPURE ALPHA-ALLOKAINOIDS, BETA-KAINOIDS, 2,3-METHANOPROLINES AND OTHER 3,4-DISUBSTITUTED PROLINES

Authors
EZQUERRA J ESCRIBANO A RUBIO A REMUINAN MJ VAQUERO JJ
Citation
J. Ezquerra et al., 4-BENZYL-2,3-DIDEHYDROPROLINATE AS A HOMOCHIRAL TEMPLATE FOR MICHAEL ADDITIONS - SYNTHESIS OF ENANTIOPURE ALPHA-ALLOKAINOIDS, BETA-KAINOIDS, 2,3-METHANOPROLINES AND OTHER 3,4-DISUBSTITUTED PROLINES, Tetrahedron : asymmetry, 7(9), 1996, pp. 2613-2626
Citations number
56
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
9
Year of publication
1996
Pages
2613 - 2626
Database
ISI
SICI code
0957-4166(1996)7:9<2613:4AAHTF>2.0.ZU;2-E
Abstract
Ethyl -N-methoxycarbonyl-4-benzyl-2,3-didehydroprolinate 10a undergoes Michael additions with stabilized carbanions and cuprates giving excl usively the enantiopure all-trans 3,4-disubstituted prolinates. The hi gh stereoselection observed in this reaction is driven by the C-4 subs tituent of the Michael acceptor. This methodology has been applied to the synthesis of the enantiopure beta-kainoid 5a and the 2,3-methanopr oline 15. Copyright (C) 1996 Elsevier Science Ltd