A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-{[}1,4]benzoxazines / Gruzdev Dmitry A.,Chulakov Evgeny N.,Levit Galina L.,Ezhikova Marina A.,Kodess Mikhail I.,Krasnov Victor P. // TETRAHEDRON-ASYMMETRY. - 2013. - V. 24, l. 19. - P. 1240-1246.

ISSN/EISSN:

0957-4166 / нет данных

Type:

Article

Abstract:

The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-{[}1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee >99\%) was developed. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

HIGHLY ENANTIOSELECTIVE HYDROGENATION; N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; ASYMMETRIC TRANSFER HYDROGENATION; ALPHA-AMINO ESTERS; HETEROCYCLIC AMINES; N-ACYLATION; CHIRAL BENZIMIDAZOLIDE; BINDING APPROACH; AROMATIC-AMINES; PI INTERACTIONS

DOI:

10.1016/j.tetasy.2013.07.024

Web of Science ID:

ISI:000326364300010

Соавторы в МНС:

—

Другие поля

Поле	Значение
Month	OCT 15
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	HIGHLY ENANTIOSELECTIVE HYDROGENATION; N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; ASYMMETRIC TRANSFER HYDROGENATION; ALPHA-AMINO ESTERS; HETEROCYCLIC AMINES; N-ACYLATION; CHIRAL BENZIMIDAZOLIDE; BINDING APPROACH; AROMATIC-AMINES; PI INTERACTIONS
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 {[}12-03-31615, 12-03-33029, 13-03-00674]; Ural Branch of RAS {[}12-P-3-1030]; State Program for Supporting of Leading Scientific Schools of the Russian Federation {[}NSh-5505.2012.3]
Funding-Text	The authors thank Liliya Sh. Sadretdinova and Dr. Andrey A. Tumashov for performing HPLC analyses, Dr. Pavel A. Slepukhin for performing X-ray crystallography analysis. The work was financially supported by the Russian Foundation for Basic Research (grants Nos. 12-03-31615, 12-03-33029, 13-03-00674); the Ural Branch of RAS (grant 12-P-3-1030) and the State Program for Supporting of Leading Scientific Schools of the Russian Federation (grant NSh-5505.2012.3).
Number-of-Cited-References	59
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	22
Journal-ISO	Tetrahedron-Asymmetry
Doc-Delivery-Number	244CI