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A Novel One‐Step Approach for the Preparation of α ‐Amino Acids, α ‐Amino Amides, and Dipeptides from Azetidine‐2,3‐diones
Author(s) -
Alcaide Benito,
Almendros Pedro,
Aragoncillo Cristina
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020816)8:16<3646::aid-chem3646>3.0.co;2-m
Subject(s) - azetidine , chemistry , amino acid , nucleophile , primary (astronomy) , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , physics , biochemistry , astronomy
A remarkable reaction of azetidine‐2,3‐diones with primary as well as secondary amines, and water is presented. Simply by varying the nucleophile, an unprecedented one‐step synthesis of α ‐amino acids, α ‐amino amides, and dipeptides, was developed in both the racemic and optically pure forms. The current mechanistic hypothesis invokes a concerted process involving CO extrusion. However, a stepwise pathway can also account for these novel transformations.