Peptide-metal complex as an asymmetric catalyst. A catalytic enantioselective cyanohydrin synthesis

Article abstract of DOI:10.1016/S0040-4039(00)92163-4

An acyclic dipeptide ester, 2-hydroxy-1-naphthylideneimino-(S)-valyl-(S)-tryptophane methyl ester (1a: Nap-S-Val-S-Trp-OMe), whose terminal amino group is modified to a Schiff base, is designed as a chiral auxiliary of an asymmetric catalyst. The mixture of 1 with titanium alkoxide catalyzes enantioselective hydrocyanation of benzaldehyde to afford optically active (R)-mandelonitrile with stereoselectivities up to 96:6.