Synthesis of enantiopure azetidine 2-carboxylic acids and their incorporation into peptides

Enantiopure azetidine 2-carboxylic acids were prepared by hydrolysis of the corresponding 2-cyano azetidines, without ring cleavage of the azetidine or epimerization. The produced amino acids, which are conformationally constrained analogues of phenylalanine, can be cleanly debenzylated and used for...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 14; no. 16; pp. 2407 - 2412
Main Authors Couty, François, Evano, Gwilherm, Rabasso, Nicolas
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.08.2003
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CONFORMATIONALLY CONSTRAINED ANALOGS
PHENYLALANINE
ASYMMETRIC-SYNTHESIS
AMINO-ACIDS
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Summary:Enantiopure azetidine 2-carboxylic acids were prepared by hydrolysis of the corresponding 2-cyano azetidines, without ring cleavage of the azetidine or epimerization. The produced amino acids, which are conformationally constrained analogues of phenylalanine, can be cleanly debenzylated and used for the synthesis of tripeptides. In the course of the synthesis of new enantiopure 2-cyano azetidines through intramolecular alkylation of a metallated amino nitrile, it was found that the involved anionic cyclisation can be thermodynamically controlled, thus enhancing its diastereoselectivity. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(03)00493-2