Trifluoromethyl vs. methyl ability to direct enantioselection in microbial reduction of carbonyl substrates.

被引:43
作者
Arnone, A
Bernardi, R
Blasco, F
Cardillo, R
Resnati, G
Gerus, II
Kukhar, VP
机构
[1] Politecn Milan, CNR, Ctr Studio Sostanze Organ Nat, Dip Chim, I-20131 Milan, Italy
[2] Ukrainian Acad Sci, Inst Bioorgan Chem & Petrochem, UA-253660 Kiev 94, Ukraine
关键词
D O I
10.1016/S0040-4020(98)83017-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective reduction of 3-trifluoromethylcyclohexanone (1a), (E)-1.1.1-trifluoro-4-phenyl-3-buten-2-one (3a). and their unfluorinated analogues 1b and 3b has been performed with some growing microorganisms. Differences in the electronic and steric properties of the trifluoromethyl and methyl residues result in different chemo- and stereoselectivities in the microbial reduction of phenylbutenones 3a and 3b while cyclohexanones 1a and 1b showed strictly similar stereoselectivities. A new protocol based on C-13 NMR spectra of 2-phenylpropionic acid esters has been used to assign the absolute configuration of the obtained secondary alcohols. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:2809 / 2818
页数:10
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