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Synfacts 2006(5): 0508-0508  
DOI: 10.1055/s-2006-934454
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Hydrobenzofuranones via Enantioselective Stetter Reaction

Contributor(s): Benjamin List, Subhas Chandra Pan
Q. Liu, T. Rovis*
Colorado State University, Fort Collins, USA
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

The Stetter reaction, a nucleophile-catalyzed addition of an aldehyde to a Michael ­acceptor, is an important transformation in organic chemistry. Here the authors report a highly enantio- and diastereoselective intramolecular Stetter reaction for the asymmetric synthesis of hydrobenzofuranones. Catalyst 1 with KHMDS has been found to be effective for the desym­metrizing Stetter reaction of a wide range of 2,4,6-trisubstituted phenol-derived cyclohexa­dienones.