Tetrahedron Letters p. 4333 - 4336 (1991)
Update date:2022-09-26
Topics: Product Formation Regeneration of Catalyst Substrate Binding Selection of Peptide Ligand Complexation with a Metal Enantioselective Transformation
Mori
Nitta
Kudo
Inoue
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.
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