Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters byMannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines

Authors
Vicario, JL Badia, D Carrillo, L
Citation
Jl. Vicario et al., Asymmetric synthesis of beta-substituted alpha-methyl-beta-amino esters byMannich reaction of (S,S)-(+)-pseudoephedrine acetamide derived enolate with imines, ORG LETT, 3(5), 2001, pp. 773-776
Citations number
68
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
5
Year of publication
2001
Pages
773 - 776
Database
ISI
SICI code
1523-7060(20010308)3:5<773:ASOBAE>2.0.ZU;2-#
Abstract
[GRAPHICS] The reaction of an (S,S)-(+)-pseudoephedrine acetamide based enolate with s everal imines afforded smoothly and with full stereochemical control a seri es of beta -substituted alpha -methyl-beta -aminoamides that upon hydrolysi s/esterification afforded the corresponding beta -aminoester derivatives in good yields and in almost enantiomerically pure form.