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Enantio‐ and Diastereoselective Chemoenzymatic Synthesis of C2‐Symmetric Biaryl‐Containing Diols
Author(s) -
Burda Edyta,
Bauer Walter,
Hummel Werner,
Gröger Harald
Publication year - 2010
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.200900156
Subject(s) - diastereomer , chemistry , diol , biphenyl , enantiomer , suzuki reaction , enantioselective synthesis , organic chemistry , combinatorial chemistry , catalysis , palladium
Abstract An enantio‐ and diastereoselective synthesis of C2‐symmetric diols bearing a biphenyl‐framework has been developed by means of an enzymatic reduction of the corresponding diketones, which were prepared by a Suzuki coupling reaction. Furthermore, a chemoenzymatic one‐pot synthesis of a C2‐symmetric diol in aqueous media has been realized through combination of the Suzuki coupling reaction and enzymatic reduction. Chiral stereoisomers of the biaryl‐containing diols are prepared with diastereomeric ratios in excess of 25:1 and enantiomeric excesses of greater than 99 %.