New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-beta-lactam

Authors
Barbaro, G Battaglia, A Di Giuseppe, F Giorgianni, P Guerrini, A Bertucci, C Geremia, S
Citation
G. Barbaro et al., New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl-beta-lactam, TETRAHEDR-A, 10(14), 1999, pp. 2765-2773
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
14
Year of publication
1999
Pages
2765 - 2773
Database
ISI
SICI code
0957-4166(19990716)10:14<2765:NESO(>2.0.ZU;2-U
Abstract
A method is described for the chiral synthesis of (3R,4S)-3-methyl-3-hydrox y-4-phenyl-beta-lactam, a useful precursor for the semi-synthesis of 2'-met hyl-taxoids. This protocol follows Seebach's synthetic principle of 'self-r egeneration of stereocenters' (SRS) and has been applied to addition reacti ons of the (2S)-chiral enolates of dioxolan-4-ones, derived from the acetal ization of (S)-alpha-lactic acid and tert-butylaldehyde or pinacolone, to N -trimethylsilylphenyl aldimine. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.