Asymmetric synthesis of γ-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes

NJ Peraino, HJ Ho, M Mondal, NJ Kerrigan - Tetrahedron Letters, 2014 - Elsevier
A method for the enantioselective synthesis of γ-lactones through the reaction of
enantioenriched sulfoxonium ylides, aldehydes, and ketenes was developed.
Enantioenriched (98% ee) aminosulfoxonium ylide was subjected to reaction with a variety
of aldehydes (both aromatic and aliphatic) and disubstituted ketenes, leading to the
formation of α, β-substituted γ-lactones in moderate to very good diastereoselectivity (dr up
to 95: 5) and with enantiomeric excesses of up to 79% ee. Best levels of enantioselectivity …
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