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Synfacts 2006(10): 1001-1001  
DOI: 10.1055/s-2006-949354
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Thiazinanes and Pyrrolidinones via Au(I)-Catalyzed Hydroamination

Contributor(s): Victor Snieckus, Heiko Scharl
X.-Y. Liu, C.-H. Li, C.-M. Che*
University of Hong Kong, P. R. of China
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

A new Au(I)-catalyzed hydroamination route to cyclic sulfonamides and pyrrolidi­nones under thermal or microwave conditions is reported. Pyrrolidinones constitute basic heterocycles for which classical methodologies are well established; however, regioselectivity due to ambident heteroatom reactivity is sometimes problematic. Among the few isolated methods available for thiazinanes are the NaOMe-induced cyclization of a 4-sulfamoyl butyric acid ester derivative (93% yield) and the intramolecular aminohydroxylation with K2OsO4 of a pent-4-enylsulfonamide (59% yield) (M. N. Kenworthy, R. J. K. Taylor Org. Biomol. Chem. 2005, 3, 603-611; A. D. Campbell, A. M. Birch Synlett 2005, 834-838). In comparison, the present method allows their synthesis in rapid and general fashion. Thia­zinanes have found use as therapeutic agents, for example, in the treatment of rheumatoid arthritis or osteoarthritis (see book below).