Synthesis of 4-amino derivatives of 5-oxoproline / Krasnov Victor P.,Vigorov Alexey Yu.,Nizova Irina A.,Matveeva Tatyana V.,Grishakov Alexander N.,Bazhovll Iliya V.,Tumashov Andrey A.,Ezhikova Marina A.,Kodess Mikhail I. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2007. - V. , l. 25. - P. 4257-4266.

ISSN/EISSN:

1434-193X / нет данных

Type:

Article; Proceedings Paper

Abstract:

The possibility of obtaining the steremsomeric 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. ((c) Wiley-VCH Verlag GmbH \& Co. KGaA, 69451 Weinheim, Germany, 2007).

Author keywords:

amino acids; nucleophilic substitution; hydrolysis; gamma-lactams; diastereoselectivity GAMMA-HYDROXYGLUTAMIC ACID; EXCITATORY AMINO-ACIDS; GLUTAMIC-ACID; NUCLEOPHILIC-SUBSTITUTION; 4-HALOGENATED DERIVATIVES; 4-AMINOPYROGLUTAMIC ACID; ASYMMETRIC-SYNTHESIS; PYROGLUTAMIC ACID; ANALOGS; STEREOISOMERS

DOI:

10.1002/ejoc.200700346

Web of Science ID:

ISI:000249391800017

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	SEP
Note	15th European Symposium on Organic Chemistry (ESOC 15), Univ Coll Dublin, Dublin, IRELAND, JUL 08-13, 2007
Publisher	WILEY-V C H VERLAG GMBH
Address	PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY
Language	English
Keywords-Plus	GAMMA-HYDROXYGLUTAMIC ACID; EXCITATORY AMINO-ACIDS; GLUTAMIC-ACID; NUCLEOPHILIC-SUBSTITUTION; 4-HALOGENATED DERIVATIVES; 4-AMINOPYROGLUTAMIC ACID; ASYMMETRIC-SYNTHESIS; PYROGLUTAMIC ACID; ANALOGS; STEREOISOMERS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	ca@ios.uran.ru
Number-of-Cited-References	42
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	3
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	209ME