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The First Gold‐Catalyzed CS Bond Formation: Cycloisomerization of α‐Thioallenes to 2,5‐Dihydrothiophenes
Author(s) -
Morita Nobuyoshi,
Krause Norbert
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.200503846
Subject(s) - cycloisomerization , stereoselectivity , ring (chemistry) , sulfur , chemistry , catalysis , scheme (mathematics) , stereochemistry , combinatorial chemistry , organic chemistry , mathematics , mathematical analysis
One good ring deserves another : A highly efficient and stereoselective cycloisomerization of α‐thioallenes to 2,5‐dihydrothiophenes is the first example of a gold‐catalyzed carbon–sulfur bond formation (see scheme, X=Cl, I). Both gold( I ) and gold( III ) salts can be used as the precatalyst, with AuCl and AuI giving the best yields. The method is of interest for the stereoselective synthesis of biologically active 2,5‐disubstituted dihydro‐ or tetrahydrothiophenes.