Formation of Disubstituted β-Lactones Using Bifunctional Catalysis
Organic Letters2005Vol. 7(9), pp. 1809–1812
Citations Over TimeTop 10% of 2005 papers
Abstract
[reaction: see text] Acid chlorides and aromatic aldehydes react in the presence of a stoichiometric amount of a tertiary amine and catalytic amounts of a cinchona alkaloid derivative and a Lewis acid to produce beta-lactones in high diastereo- and enantioselectivity. The sense of the diastereoselectivity depends on the substitution of the acid chloride, with the reactions of aliphatic acid chlorides giving predominantly the trans-isomer and those of alkoxyacetyl chlorides favoring formation of the cis-isomer.
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