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Short Paper | Special issue | Vol 97, No. 2, 2018, pp.1269-1287
Published online, 18th May, 2018
DOI: 10.3987/COM-18-S(T)86
Direct Enantioselective Indolylation of Peptidyl Imine for the Synthesis of Indolyl Glycine-Containing Peptides

Tsubasa Inokuma, Kodai Nishida, Akira Shigenaga, Ken-ichi Yamada, and Akira Otaka*

*Graduate School of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan


A novel synthetic method involving the direct application of a catalytic asymmetric reaction to peptides was developed. The conditions optimized for the model asymmetric reaction of a simple α-imino amide with an indole derivative were successfully applied to an asymmetric Friedel–Crafts reaction of α-imino peptide possessing a hydrophobic anchor to afford the indolyl glycine-containing peptide. This novel strategy will be of great value for the synthesis of the biologically important peptides bearing varieties of unnatural amino acids.