The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effectivechiral auxiliary for conjugate additions: Asymmetric synthesis of (-)-aplysillamide B.

Authors
Davies, SG Sanganee, HJ Szolcsanyi, P
Citation
Sg. Davies et al., The 'SuperQuat' (R)-4-phenyl-5,5-dimethyl oxazolidin-2-one as an effectivechiral auxiliary for conjugate additions: Asymmetric synthesis of (-)-aplysillamide B., TETRAHEDRON, 55(11), 1999, pp. 3337-3354
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
11
Year of publication
1999
Pages
3337 - 3354
Database
ISI
SICI code
0040-4020(19990312)55:11<3337:T'(OAA>2.0.ZU;2-S
Abstract
(R)-4-Phenyl-5,5-dimethyl-oxazolidin-2-one, readily available from D-phenyl glycine, is shown to be an effective chiral auxiliary for stereoselective c onjugate additions to attached alpha,beta-unsaturated N-acyl moieties. Its utility is demonstrated by the asymmetric synthesis of the antifungal, anti bacterial (-)-Aplysillamide B. (C) 1999 Elsevier Science Ltd. All rights re served.