PREPARATION OF ENANTIOENRICHED ALPHA-SILYL-BENZYLCARBAMATES

Authors
BARBERIS C VOYER N
Citation
C. Barberis et N. Voyer, PREPARATION OF ENANTIOENRICHED ALPHA-SILYL-BENZYLCARBAMATES, Tetrahedron letters, 39(38), 1998, pp. 6807-6810
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
38
Year of publication
1998
Pages
6807 - 6810
Database
ISI
SICI code
0040-4039(1998)39:38<6807:POEA>2.0.ZU;2-8
Abstract
The first examples of an enantioselective [1,2] silicon rearrangement are reported. This novel synthetic method lead to the formation of chi ral alpha-substituted benzylamines with an alpha-silyl group. In the p rocedure, N-Silyl-protected N-Boc benzylamines are subjected to enanti oselective deprotonation using the chiral complex (-) sparteine.s-Buli to generate chiral benzyllithium intermediates that undergo a [1,2] s ilicon shift. (C) 1998 Elsevier Science Ltd. All rights reserved.