Structurally rigid, chiral spiro ammonium salts of type (R, R)- or (S, S)-1 derived from commercially available (R)- or (S)-1, 1′-bi-2-naphthol have been designed as new C₂-symmetric chiral phase transfer catalysts and successfully applied to the highly efficient, catalytic enantioselective alkylation of tert-butyl glycinate Schiff base under mild phase transfer conditions to furnish α-alkyl-α-amino acids and α, α-dialkyl-α-amino acids with excellent enantioselectivity. These catalysts have been also utilized for the asymmetric terminal functionallization of peptides and asymmetric direct aldol reaction of glycine derivative.

(Communicated by Hitosi NOZAKI, M. J. A., Sept. 12, 2003)