Asymmetric access to peptidyl beta(3)-aldehydes by coupling of N-phthalyl alpha-amino acids with a synthetic heterocyclic beta-amino aldehyde precursor

摘要

Asymmetric access to novel N-protected (di)peptidyl beta(3)-aldehydes ("beta(3)-PAs") has been achieved through direct coupling of a chiral non-racemic 6-alkoxytetrahydrooxazinone with N-phthalyl L-G-amino acids. Kinetic resolution allows for the fruitful use of racemic amino acids in this process. Acidic hydrolysis of the diastereomerically pure, coupling products leads to the title N-phthalyl-beta(3)-PAs in high yields. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).