Enantioselective Synthesis of Tertiary Alcohols by the Desymmetrizing Benzoylation of 2-Substituted Glycerols

Complementary catalysts have been found for the enantioselective desymmetrization of 2‐substituted glycerols by monobenzoylation with benzoyl chloride and Et3N to give chiral tertiary alcohols with 80 to 94 % ee (see Scheme; Bn=benzyl, Bz=benzoyl). The dibenzylbisoxazoline–CuCl2 complex 1 is remarka...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2007-04, Vol.46 (15), p.2616-2618
Main Authors: Jung, Byunghyuck, Hong, Mi Sook, Kang, Sung Ho
Format: Article
Language:English
Subjects:
asymmetric catalysis
benzoylation
desymmetrization
enantioselectivity
tertiary alcohols
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Summary:Complementary catalysts have been found for the enantioselective desymmetrization of 2‐substituted glycerols by monobenzoylation with benzoyl chloride and Et3N to give chiral tertiary alcohols with 80 to 94 % ee (see Scheme; Bn=benzyl, Bz=benzoyl). The dibenzylbisoxazoline–CuCl2 complex 1 is remarkably effective for substrates with an alkyl substituent in the 2‐position, the iminooxazoline–CuCl2 complex 2 for those with vinyl, phenyl, and benzyl substituents.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200604977