THE PRODUCT OF BAKERS-YEAST REDUCTION OF ETHYL 2-CHLORO-3-OXOBUTANOATE AS A PRECURSOR OF THE 1-ETHOXYCARBONYL 2(S)-HYDROXYPROPYL RADICAL

Authors
HAMDANI M DEJESO B DELEUZE H SAUX A MAILLARD B
Citation
M. Hamdani et al., THE PRODUCT OF BAKERS-YEAST REDUCTION OF ETHYL 2-CHLORO-3-OXOBUTANOATE AS A PRECURSOR OF THE 1-ETHOXYCARBONYL 2(S)-HYDROXYPROPYL RADICAL, Tetrahedron : asymmetry, 4(6), 1993, pp. 1233-1236
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
6
Year of publication
1993
Pages
1233 - 1236
Database
ISI
SICI code
0957-4166(1993)4:6<1233:TPOBRO>2.0.ZU;2-P
Abstract
Baker's yeast treatment of ethyl 2-chloro-3-oxobutanoate 1, diethyl 2- acetylmalonate 2 and ethyl 2-cyano-3-oxobutanoate 3 was effected in or der to obtain enantiomerically enriched compounds. In contrast to the reaction of 2 and 3, efficient diastereo- and enantioselective reducti on of 1 provided ethyl 2(R)-chloro-3(S)-hydroxybutanoate. This product was used as precursor of the 1-ethoxycarbonyl-2(S)-hydroxypropyl radi cal and the diastereoselectivity of the addition of this intermediate to alkenes was studied.