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Calter, M.A. et al.

Calter, Tretyak, Flaschenriem,

Formation of disubstituted beta-lactones using bifunctional catalysis.

[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.[1]

References

Formation of disubstituted beta-lactones using bifunctional catalysis. Calter, M.A., Tretyak, O.A., Flaschenriem, C. Org. Lett. (2005) [Pubmed]

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