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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 409-414

Dual Lewis acid - Lewis base activation in enantioselective additions to aldehydes

Erica Wingstrand, Stina Lundgren, Maël Penhoat and Christina Moberg

Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE 100 44 Stockholm, Sweden

Abstract: Reaction of benzaldehyde with ethyl cyanoformate in the presence of Lewis acidic Ti(IV) complexes of bispyridylamide or salen ligands and Lewis basic amines affords the O-alkoxycarbonylated cyanohydrin. In the presence of the salen-based catalytic system, acetyl cyanide can also be added to benzaldehyde, providing a highly enantioselective direct route to the O-acetylated cyanohydrin.