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.
Calter
Michael A
MA
Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459-0180, USA. mcalter@wesleyan.edu
Tretyak
Olexandr A
OA
Flaschenriem
Christine
C
D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D007783:Lactones