BAKERS-YEAST REDUCTION OF (E)-1-PHENYL-1,2-PROPANEDIONE 2-(O-METHYLOXIME) - A KEY STEP FOR A (-)-NOREPHEDRINE SYNTHESIS

Authors
KREUTZ OC MORAN PJS RODRIGUES JAR
Citation
Oc. Kreutz et al., BAKERS-YEAST REDUCTION OF (E)-1-PHENYL-1,2-PROPANEDIONE 2-(O-METHYLOXIME) - A KEY STEP FOR A (-)-NOREPHEDRINE SYNTHESIS, Tetrahedron : asymmetry, 8(15), 1997, pp. 2649-2653
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
15
Year of publication
1997
Pages
2649 - 2653
Database
ISI
SICI code
0957-4166(1997)8:15<2649:BRO(2>2.0.ZU;2-Q
Abstract
The enantioselective Baker's yeast reduction of (E)-1-phenyl-1,2 propa nedione 2-(O-methyloxime) 1 afforded (-)-(R)-1-hydroxy-1-phenyl-2-prop anone 2-(O-methyloxime) 2 with 97% of enantiomeric excess (ee) which w as diastereoselectively reduced by LiAlH4 to obtain the (-)-(R,S)-nore phedrine with ee=82% and (-)-(R,R)-norpseudoephedrine with ee=93% in a ratio 4:1 respectively. (C) 1997 Elsevier Science Ltd.