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From Aryl Bromides to Enantioenriched Benzylic Alcohols in a Single Flask: Catalytic Asymmetric Arylation of Aldehydes
Author(s) -
Kim Jeung Gon,
Walsh Patrick J.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200600741
Subject(s) - aryl , catalysis , chemistry , organic chemistry , combinatorial chemistry , alkyl
Stop that achiral catalyst! Chiral Lewis acid catalyzed aryl additions to aldehydes that originate from aryl halides generate products with very low ee values (see scheme, left), because the achiral metal halide by‐products are much more efficient catalysts than those derived from chiral amino alcohols. A LiCl‐selective inhibitor is introduced that enables a highly enantioselective one‐pot arylation of aldehydes that begins with aryl bromides (right).