SELECTIVE DEPROTECTION STRATEGIES TO N-(ALPHA-METHYLBENZYL)-BETA-AMINO ESTERS AND DERIVED BETA-LACTAMS

Authors
DAVIES SG ICHIHARA O
Citation
Sg. Davies et O. Ichihara, SELECTIVE DEPROTECTION STRATEGIES TO N-(ALPHA-METHYLBENZYL)-BETA-AMINO ESTERS AND DERIVED BETA-LACTAMS, Tetrahedron letters, 39(33), 1998, pp. 6045-6048
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
33
Year of publication
1998
Pages
6045 - 6048
Database
ISI
SICI code
0040-4039(1998)39:33<6045:SDSTN>2.0.ZU;2-V
Abstract
A variety of N,N-diprotected beta-amino esters, prepared by highly dia stereoselective conjugate addition of chiral lithium amides, were sele ctively mono-deprotected under-either reductive (hydrogenolysis) or ox idative (DDQ or CAN) conditions. Combined with these deprotection meth ods, lithium (alpha-methylbenzyl)(3,4-dimethoxybenzyl) amide 2 can be used as an efficient differentially protected chiral ammonia equivalen t for the asymmetric synthesis of beta-amino acid and beta-lactam deri vatives. (C) 1998 Elsevier Science Ltd. All rights reserved.