Highly stereoselective N-terminal functionalization of small peptides by chiral phase-transfer catalysis.

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Virtually complete chirality transfer has been realized in the N-terminal alkylation of small, Schiff-base activated peptides under mild phase-transfer conditions, in which finely tuned chiral quaternary ammonium salts are used as catalysts. Repeated extension and alkylation of the N-terminal position can lead selectively to nonnatural oligopeptides (see picture).