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Enantioselective Microbial Reduction of 5‐Acetylisoxazolines – A Novel Method for Stereochemical Control on Yeast Reduction
Author(s) -
Ticozzi Calimero,
Zanarotti Antonio
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890299
Subject(s) - chemistry , yeast , enantioselective synthesis , kinetic resolution , stereoselectivity , alcohol , ketone , reduction (mathematics) , kinetics , aspergillus niger , organic chemistry , stereochemistry , catalysis , biochemistry , physics , geometry , quantum mechanics , mathematics
The kinetics and the stereoselectivity of the reduction by baker′s yeast of racemic 5‐acetyl‐4,5‐dihydro‐3‐phenylisoxazole 1 to the corresponding alcohol in 2‐propanol/water mixtures are strongly dependent from the 2‐propanol/water ratio; at a ratio of 4.0, the reduction allows a kinetic resolution leading to alcohol 2 and ketone ( R )‐ 1 Subsequent reduction of ( R )‐ 1 with yeast in water and with Aspergillus niger leads to alcohols 3 and 4 with high ee.