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Asymmetric Access to Peptidyl β 3 ‐Aldehydes by Coupling of N ‐Phthalyl α‐Amino Acids with a Synthetic Heterocyclic β‐Amino Aldehyde Precursor
Author(s) -
Yin Biaolin,
Dhal Robert,
Maisonneuve Vincent,
Dujardin Gilles
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600262
Subject(s) - chemistry , aldehyde , hydrolysis , kinetic resolution , amino acid , coupling (piping) , organic chemistry , enantioselective synthesis , catalysis , biochemistry , mechanical engineering , engineering
Asymmetric access to novel N ‐protected (di)peptidyl β 3 ‐aldehydes (“β 3 ‐PAs”) has been achieved through direct coupling of a chiral non‐racemic 6‐alkoxytetrahydrooxazinone with N ‐phthalyl L ‐α‐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‐β 3 ‐PAs in high yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)