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Vanadium‐Catalyzed Sulfur Oxidation/Kinetic Resolution in the Synthesis of Enantiomerically Pure Alkyl Aryl Sulfoxides
Author(s) -
Drago Carmelo,
Caggiano Lorenzo,
Jackson Richard F. W.
Publication year - 2005
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.200503046
Subject(s) - vanadium , alkyl , aryl , kinetic resolution , catalysis , chemistry , enantioselective synthesis , sulfur , sulfoxide , ligand (biochemistry) , solvent , organic chemistry , chloroform , biochemistry , receptor
The importance of the mix : The use of chloroform as solvent, the ligand ( R )‐ 2 and [VO(acac) 2 ] as catalyst, and H 2 O 2 as oxidant promotes the highly enantioselective oxidation of simple alkyl aryl sulfides 1 to give alkyl aryl sulfoxides ( R )‐ 3 (see scheme). The success of this process partly derives from an efficient kinetic resolution of the product sulfoxides.