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DOI: 10.1055/s-0029-1219104
Aldol Process Catalyzed by Chiral Tin Methoxides
A. Yanagisawa*, T. Satou, A. Izumiseki, Y. Tanaka, M. Miyagi, T. Arai, K. Yoshida
Chiba University, Japan
Publikationsverlauf
Publikationsdatum:
21. Januar 2010 (online)
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Significance
The importance of the catalytic asymmetric aldol reaction can hardly be overestimated. Among numerous existing methods there are, however, few examples of enantioselective aldol reaction proceeding via a chiral metal enolate. The authors previously found that Bu2Sn(OMe)2 catalyzes the reaction between alkenyl trichloroacetates and aldehydes in the presence of methanol. In this paper they expand this methodology to a chiral version using chiral tin methoxide formed in situ from dibromide 2. The use of 10 mol% of catalyst furnished a number of acyclic products with yields of 41-80% and high enantioselectivities (88-99%). The diastereoselectivity ranged from 85:15 to >99:1. A number of cyclic substrates were also employed with moderate success.