Chirality Transfer from Epoxide to Carbanion: Base-Induced Alkylation of O-Carbamoyl Cyanohydrins of β-Silyl-α,β-epoxy Aldehyde

Enantioselective C–C bond formation at an α-position of a nitrile group with an external electrophile can be realized, although in modest ee, with the aid of both the concerted process of an epoxysilane rearrangement and a carbamoyl group. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)