Enantioselective conjugate addition of aliphatic thiols to divergently activated electron poor alkenes and dienes

Divergently activated double bonds in electron poor 4-oxo-butenoates and (2E,4E)-6-oxo-2,4-dienoates underwent stereoselective and regioselective addition of mercaptans catalyzed by simple Cinchona alkaloids. Application of quinine and quinidine afforded both enantiomers of the 1,4-adducts with respect to the ketone carbonyl group in ees of up to 80%. Single recrystallization of some adducts resulted in further enrichment of up to 99%ee.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide