Abstract
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.
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