Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides / Levit Galina L.,Gruzdev Dmitry A.,Krasnov Victor P.,Chulakov Evgeny N.,Sadretdinova Liliya Sh,Ezhikova Marina A.,Kodess Mikhail I.,Charushin Valery N. // TETRAHEDRON-ASYMMETRY. - 2011. - V. 22, l. 2. - P. 185-189.

ISSN/EISSN:

0957-4166 / нет данных

Type:

Article

Abstract:

The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe > H > NO(2)) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution. (C) 2010 Elsevier Ltd. All rights reserved.

Author keywords:

CATALYZED KINETIC RESOLUTION; AROMATIC INTERACTIONS; AGENT; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE; TRANSFORMATION; RECOGNITION; ALKALOIDS; ACIDS

DOI:

10.1016/j.tetasy.2010.12.017

Web of Science ID:

ISI:000288890800010

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 31
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	CATALYZED KINETIC RESOLUTION; AROMATIC INTERACTIONS; AGENT; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE; TRANSFORMATION; RECOGNITION; ALKALOIDS; ACIDS
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, 09-1-3-2004]; {[}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 09-1-3-2004). The authors thank the Ural Division of RAS for financial support for D.A.G. and E.N.C.
Number-of-Cited-References	43
Usage-Count-Since-2013	6
Journal-ISO	Tetrahedron-Asymmetry
Doc-Delivery-Number	741UN