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Enantioselective Benzylic Hydroxylation with Pseudomonas monteilii TA‐5: A Simple Method for the Syntheses of ( R )‐Benzylic Alcohols Containing Reactive Functional Groups
Author(s) -
Chen Yongzheng,
Lie Felicia,
Li Zhi
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900241
Subject(s) - enantioselective synthesis , chemistry , hydroxylation , yield (engineering) , biocatalysis , functional group , organic chemistry , stereochemistry , catalysis , reaction mechanism , enzyme , materials science , polymer , metallurgy
Highly enantioselective benzylic hydroxylations of benzene derivatives ( 1–4 ) containing reactive functional groups were achieved for the first time with Pseudomonas monteilii TA‐5 as biocatalyst, giving the corresponding ( R )‐benzylic alcohols 5 – 8 in 93–99% ee as the only products. Preparative biotransformations were demonstrated by the biohydroxylation of 1 and 2 with resting cells of P. monteilii TA‐5 to afford ( R )‐ 5 in 94% ee and 66% yield and ( R )‐ 6 in 94% ee and 56% yield, respectively. The highly enantioselective biohydroxylations represent a simple access to ( R )‐benzylic alcohols containing reactive functional groups that are useful pharmaceutical intermediates and versatile chiral building blocks.