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In this manuscript a new organocatalytic approach to spirocyclic tetrahydrothiophenes bearing either a butenolide or an azlactone moiety is described. The developed methodology is based on the cascade reactivity of 2-mercaptoacetaldehyde (generated in situ from 1,4-dithiane-2,5-diol) with α,β-unsaturated butenolides or azlactones, that consists of a thio-Michael addition followed by an intramolecular aldol reaction. Chiral bases derived from cinchona alkaloids are used as a catalyst promoting the cascade and controlling its stereochemical outcome.

Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif