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Full Paper
Synthesis of 4-Amino Derivatives of 5-Oxoproline
Article first published online: 10 JUL 2007
DOI: 10.1002/ejoc.200700346
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Krasnov, V. P., Vigorov, A. Yu., Nizova, I. A., Matveeva, T. V., Grishakov, A. N., Bazhov, I. V., Tumashov, A. A., Ezhikova, M. A. and Kodess, M. I. (2007), Synthesis of 4-Amino Derivatives of 5-Oxoproline. Eur. J. Org. Chem., 2007: 4257–4266. doi: 10.1002/ejoc.200700346
Publication History
- Issue published online: 10 AUG 2007
- Article first published online: 10 JUL 2007
- Manuscript Received: 19 APR 2007
Funded by
- Russian Foundation for Basic Research. Grant Number: 06-03-32791
- State Program for Supporting of Leading Scientific Schools of the Russian Federation. Grant Number: NSh 9178.2006.3
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- Cited By
Keywords:
- Amino acids;
- Nucleophilic substitution;
- Hydrolysis;
- γ-Lactams;
- Diastereoselectivity
Abstract
The possibility of obtaining the stereoisomeric derivatives of 5-oxoproline and glutamic acid with a tertiary amino group at C-4, using the nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloylglutamate with secondary amines followed by resolution of diastereomers and removal of protecting groups has been studied. We have shown that the reaction with arylamines results in optically pure 5-oxoproline derivatives in high yields. In the case of more basic amines, the reaction is accompanied by racemization, and the target products can be isolated only as diastereomeric racemates.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)