Formation of disubstituted beta-lactones using bifunctional catalysis |
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Authors: | Calter Michael A Tretyak Olexandr A Flaschenriem Christine |
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Affiliation: | Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459-0180, USA. mcalter@wesleyan.edu |
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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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