Enantioselective synthesis of beta-hydroxy carboxylic acids: direct conversion of beta-oxocarboxylic acids to enantiomerically enriched beta-hydroxy carboxylic acids via neighboring group control

Authors
Wang, Z Zhao, CL Pierce, ME Fortunak, JM
Citation
Z. Wang et al., Enantioselective synthesis of beta-hydroxy carboxylic acids: direct conversion of beta-oxocarboxylic acids to enantiomerically enriched beta-hydroxy carboxylic acids via neighboring group control, TETRAHEDR-A, 10(2), 1999, pp. 225-228
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
2
Year of publication
1999
Pages
225 - 228
Database
ISI
SICI code
0957-4166(19990129)10:2<225:ESOBCA>2.0.ZU;2-Y
Abstract
beta-Oxocarboxylic acids can be reduced to the corresponding beta-hydroxy c arboxylic acids employing DIP-Cl(TM) as a reducing agent. The beta-carboxyl ic substituent exerts a remarkable neighboring group effect on the reductio n. The reaction presumably proceeds in an intramolecular fashion through a 'rigid' bicyclic transition state assembly, which produces enantioselectivi ties approaching 99%. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.