학술논문

Catalytic asymmetric synthesis of α-amino acid derivatives and peptides using chiral phase-transfer catalysts
Document Type
Journal Article
Author
Source
Proceedings of the Japan Academy, Series B. 2003, 79B(7):181
Subject
Phase transfer catalyst
aldol
asymmetric alkylation
tert-butyl glycinate
α-amino acid
Language
English
ISSN
0386-2208
1349-2896
Abstract
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)