Lipase-catalyzed enantioselective desymmetrization of prochiral 3,3-bis(hydroxymethyl)oxindoles

Article abstract of DOI:10.1016/S0040-4039(01)01547-7

Oxindoles 3b-d (91-98% ee) having a chiral quaternary carbon center at the C-3 position were prepared from readily available oxindoles 5a-c in 50-64% overall yields, in which an enantioselective desymmetrization of prochiral 1,3-diols 2b-d using a Candida rugosa lipase (Meito OF) and 1-ethoxyvinyl 2-furoate 1 was employed as the key step.