Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides / Gruzdev Dmitry A.,Levit Galina L.,Krasnov Victor P.,Chulakov Evgeny N.,Sadretdinova Liliya Sh.,Grishakov Aleksandr N.,Ezhikova Marina A.,Kodess Mikhail I.,Charushin Valery N. // TETRAHEDRON-ASYMMETRY. - 2010. - V. 21, l. 8. - P. 936-942.

ISSN/EISSN:

0957-4166 / нет данных

Type:

Article

Abstract:

A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)phenylalanyl chloride proved to be the most appropriate chiral acylating agent. (C) 2010 Elsevier Ltd. All rights reserved.

Author keywords:

HETEROCYCLIC AMINES; ACIDS; AGENT; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE; CATALYST

DOI:

10.1016/j.tetasy.2010.05.013

Web of Science ID:

ISI:000280120700009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR 30
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	HETEROCYCLIC AMINES; ACIDS; AGENT; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE; CATALYST
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic; Chemistry, Physical
Author-Email	ca512@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}10-03-00084]; Russian Federation {[}NSh 65261.2010.3]; Ural Division of RAS {[}09-P-3-2001, 09-I-3-2004]; {[}02.522.12.2011]
Funding-Text	The work was financially supported by the Russian Foundation for Basic Research (Grant 10-03-00084), the State Program for Supporting of Leading Scientific Schools of the Russian Federation (Grant NSh 65261.2010.3), the State Contract No. 02.522.12.2011 and by the Ural Division of RAS (Grants 09-P-3-2001 and 09-I-3-2004). The authors thank Dr. Pavel Slepukhin for taking X-ray crystallography analyses.
Number-of-Cited-References	31
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	13
Journal-ISO	Tetrahedron-Asymmetry
Doc-Delivery-Number	628LG