Synthesis of optically-active benzylic amines; asymmetric reduction of ketoxime ethers with chiral oxazaborolidines

Authors
Fontaine, E Namane, C Meneyrol, J Geslin, M Serva, L Roussey, E Tissandie, S Maftouh, M Roger, P
Citation
E. Fontaine et al., Synthesis of optically-active benzylic amines; asymmetric reduction of ketoxime ethers with chiral oxazaborolidines, TETRAHEDR-A, 12(15), 2001, pp. 2185-2189
Citations number
9
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
15
Year of publication
2001
Pages
2185 - 2189
Database
ISI
SICI code
0957-4166(20010829)12:15<2185:SOOBAA>2.0.ZU;2-V
Abstract
The preparation of novel optically active benzylic amines by the enantio se lective reduction of phenone oximes using chiral oxazaborolidine is describ ed. The choice of the chiral 1,2-amino alcohol (S)-diphenylvalinol as chira l inducer and that of the benzyl group for the O-oxime substituent is expla ined. 23 primary amines are obtained, with high enantio selectivity (e.e. = 98%), good yield (74%) on preparative scale. A mechanistic explanation is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.