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Tandem enzyme‐catalysed reduction/ cis ‐dihydroxylation of 2,2,2‐trifluoroace‐ tophenone: chemoenzymatic routes to new enantiopure phenol and benzylic alcohol reagents
Author(s) -
Boyd Derek R.,
Sharma Narain D.,
Ljubez Vera,
Malone John F.,
Allen Christopher C. R.
Publication year - 2007
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.1686
Subject(s) - enantiopure drug , dihydroxylation , chemistry , phenols , enantiomer , phenol , ketone , organic chemistry , metabolite , alcohol , alcohol dehydrogenase , kinetic resolution , pseudomonas putida , enzyme , enantioselective synthesis , catalysis , biochemistry
Factors that control the competition between toluene dioxgenase‐catalysed arene cis ‐dihydroxylation and dehydrogenase‐catalysed ketone reduction have been studied, using whole cells of Pseudomonas putida UV and three alkylaryl ketones. The triol metabolite, obtained from 2,2,2‐trifluoroacetophenone, has been used in the synthesis of single enantiomer chiral phenols and benzylic alcohols. Potential applications of the methylether derivatives of the chiral phenols and benzylic alcohols, as resolving agents, have been found. Copyright © 2007 Society of Chemical Industry