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Synfacts 2010(4): 0475-0475  
DOI: 10.1055/s-0029-1219512
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Vinylogous Aldol Reaction of Furanones

Contributor(s): Benjamin List, Frank Lay
H. Ube, N. Shimada, M. Terada*
Tohoku University, Sendai, Japan
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

The axially chiral guanidine base catalyst 1 catalyzes an enantioselective direct vinylogous aldol reaction in high yields, moderate diastereoselectivity, and excellent enantioselectivity. Halogenated or α-thio-substituted furanones 2 are employed as the vinylogous nucleophile, instead of commonly used 2-silyloxyfuranes.