Asymmetric trimethylsilylcyanation of aldehydes utilizing chiral bismuth compounds. A frontier in bismuth mediated synthetic reactions

Article abstract of DOI:10.1016/S0957-4166(97)00570-3

Bismuth(III) chloride (BiCl₃) was found to work efficiently as a versatile catalyst for cyanation of aldehydes with trimethylsilyl cyanide to afford the corresponding cyanohydrins in high yields. Triphenylbismuthan (Ph₃Bi) is also effective. The reaction has been applied to the asymmetric cyanation of a variety of aldehydes in high yields with moderate to good enantioselectivities by use of a chiral bismuth catalyst prepared in situ from BiCl₃ and (2R,3R)-(+)-diethyl tartrate.