ASYMMETRIC REDUCTION OF KETOXIME ETHERS TO OPTICALLY-ACTIVE O-SUBSTITUTED HYDROXYLAMINES WITH REAGENTS PREPARED FROM BORANE AND CHIRAL AMINO-ALCOHOLS

Authors
DOUGHERTY JT FLISAK JR HAYES J LANTOS I LIU L TUCKER L
Citation
Jt. Dougherty et al., ASYMMETRIC REDUCTION OF KETOXIME ETHERS TO OPTICALLY-ACTIVE O-SUBSTITUTED HYDROXYLAMINES WITH REAGENTS PREPARED FROM BORANE AND CHIRAL AMINO-ALCOHOLS, Tetrahedron : asymmetry, 8(4), 1997, pp. 497-499
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
4
Year of publication
1997
Pages
497 - 499
Database
ISI
SICI code
0957-4166(1997)8:4<497:AROKET>2.0.ZU;2-3
Abstract
The asymmetric reduction of ketoxime ethers to yield enantiomerically enriched chiral hydroxylamines with reagents prepared from borane and norephedrine has been investigated. Very high enantioselectivity (ca. 99% ee) was obtained in the reduction of ketoxime O-(o-nitrobenzyl) et her to O-(o-nitrobenzyl) hydroxylamine. (C) 1997 Elsevier Science Ltd.