Enantioselective trimethylsilylcyanation of benzaldehyde using pyrrolidine-based chiral salen ligands

Abstract

The in situ formed Ti(IV) complexes of several pyrrolidine-based chiral salen ligands derived from natural (L)-tartaric acid were evaluated as catalysts in the enantioselective trimethylsilylcyanation of benzaldehyde. The catalysts were found to be very active, producing the corresponding product, O-trimethylsilylmandelonitrile, in high yields (>94%) and enantioselectivities of up to 88%.