Asymmetric Cyanohydrin Synthesis Catalyzed by Al(salen)/Triphenylphosphane Oxide

Abstract

Abstract Various aldehydes undergo asymmetric trimethylsilylcyanation with (CH 3 ) 3 SiCN (TMSCN) in the presence of a chiral Al(salen) complex and Ph 3 PO as the catalyst. This is a double activation where Al(salen) plays the role of Lewis acd and POPh 3 acts as a Lewis base. Various kind of aldehydes were subjected to the enantioselective addition of (CH 3 ) 3 SiCN at temperatures between –40 °C and –50 °C. Hydrolysis of the adducts gave cyanohydrins with over 90 % yield and 80 % ee in most cases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)