N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines / Gruzdev D. A.,Vakarov S. A.,Levit G. L.,Krasnov V. P. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2014. - V. 49, l. 12. - P. 1795-1807.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-{[}1,4]benzoxazine was developed.

Author keywords:

amines; (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-{[}1,4] benzoxazine; N-tosyl-(S)-proline; acylation; diastereoisomers; kinetic resolution; stereoselectivity N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; ALCOHOLS; DERIVATIVES; ACYLATION; CATALYSTS; DIHYDROBENZOXAZINES; DIAZIRIDINES; NITROGEN

DOI:

10.1007/s10593-014-1432-4

Web of Science ID:

ISI:000332599200011

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	MAR
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; ALCOHOLS; DERIVATIVES; ACYLATION; CATALYSTS; DIHYDROBENZOXAZINES; DIAZIRIDINES; NITROGEN
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	gruzdev-da@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}12-03-31615, 12-03-33029, 13-03-00674]; Ural Branch of the Russian Academy of Sciences {[}12-P-3-1030]; Grants Council of the President of the Russian Federation {[}NSh-3656.2014.3]
Funding-Text	The work was performed with financial support from the Russian Foundation for Basic Research (grants 12-03-31615, 12-03-33029, 13-03-00674), the Ural Branch of the Russian Academy of Sciences (project 12-P-3-1030), and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).
Number-of-Cited-References	53
Usage-Count-Since-2013	17
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	AC5ZJ