Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride / Vakarov Sergey A.,Gruzdev Dmitry A.,Chulakov Evgeny N.,Sadretdinova Liliya Sh.,Tumashov Andrey A.,Pervova Marina G.,Ezhikova Marina A.,Kodess Mikhail I.,Levit Galina L.,Krasnov Victor P.,Charushin Valery N. // TETRAHEDRON-ASYMMETRY. - 2016. - V. 27, l. 24. - P. 1231-1237.

ISSN/EISSN:

0957-4166 / нет данных

Type:

Article

Abstract:

The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-{[}1,4] benzoxazines, 3,4-dihydro-3-methyl-2H-{[}1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-{[}1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-{[}1,4]benzothiazine (99.4\% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; N-TOSYL-(S)-PROLYL CHLORIDE; DIASTEREOSELECTIVE ACYLATION; EFFICIENT; AGONIST

DOI:

10.1016/j.tetasy.2016.10.004

Web of Science ID:

ISI:000389111200005

Соавторы в МНС:

Другие поля

Поле	Значение
Month	DEC 31
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; N-TOSYL-(S)-PROLYL CHLORIDE; DIASTEREOSELECTIVE ACYLATION; EFFICIENT; AGONIST
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic; Chemistry, Physical
Author-Email	ca512@ios.uran.ru
ORCID-Numbers	Kodess, Mikhail/0000-0003-4649-3659
Funding-Acknowledgement	Russian Science Foundation {[}14-13-01077]
Funding-Text	The authors thank Dr. Pavel A. Slepukhin for performing X-ray diffraction and Dr. Ilya N. Ganebnykh for recording HRMS spectra. The work was financially supported by the Russian Science Foundation (grant 14-13-01077).
Number-of-Cited-References	33
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	10
Journal-ISO	Tetrahedron-Asymmetry
Doc-Delivery-Number	ED8GY