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Synthesis 2011(23): 3908-3914  
DOI: 10.1055/s-0031-1289578
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Unsymmetrical Polysubstituted Pyridines from β-Sulfonylvinylamines via 1-Aza-Allyl Anion Intermediates

Chan Lau, Gavin Chit Tsui, Mark Lautens*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada
Fax: +1(416)9468185 ; e-Mail: mlautens@chem.utoronto.ca;
Further Information

Publication History

Received 25 September 2011
Publication Date:
27 October 2011 (online)

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Abstract

A modular synthesis of highly functionalized unsymmetrical pyridines has been developed from reacting β-sulfonylvinylamines with α,β-unsaturated systems in the presence of base via the formation of 1-aza-allyl anion intermediates.

Key words

β-sulfonylvinylamines - 2,4,6-triarylpyridines - 1-aza-allyl anions - α,β-unsaturated ketones - cascade reactions

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12

See Supporting Information for additional details relating to the optimization process.