Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-{[}1,4]benzoxazines with 2-phenoxy carbonyl chlorides / Vakarov Sergey A.,Gruzdev Dmitry A.,Sadretdinova Liliya Sh.,Chulakov Evgeny N.,Pervova Marina G.,Ezhikova Marina A.,Kodess Mikhail I.,Levit Galina L.,Krasnov Victor P. // TETRAHEDRON-ASYMMETRY. - 2015. - V. 26, l. 5-6. - P. 312-319.

ISSN/EISSN:

0957-4166 / нет данных

Type:

Article

Abstract:

In the search for novel efficient chiral resolving agents, we have studied the diastereoselective acylation of 3,4-dihydro-3-methyl-2H-{[}1,4]benzoxazine and 7,8-difluoro-3,4-dihydro-3-methyl-2H-{[}1,4]benzoxazine with acyl chlorides of 2-phenoxy carboxylic acids (2-phenoxypropionic, 2-phenoxyisovaleric, and 2-phenoxy-3-phenylpropionic) in toluene and dichloromethane at different temperatures. HPLC analysis of the acylation products showed the predominant formation of (R{*

Author keywords:

RACEMIC HETEROCYCLIC AMINES; N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; ENANTIOSELECTIVE N-ACYLATION; KINETIC RESOLUTION; N-TOSYL-(S)-PROLYL CHLORIDE; OPTICAL RESOLUTION; CARBOXYLIC-ACIDS; ALCOHOLS; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE

DOI:

10.1016/j.tetasy.2015.02.004

Web of Science ID:

ISI:000352671600010

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	MAR 28
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	RACEMIC HETEROCYCLIC AMINES; N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; ENANTIOSELECTIVE N-ACYLATION; KINETIC RESOLUTION; N-TOSYL-(S)-PROLYL CHLORIDE; OPTICAL RESOLUTION; CARBOXYLIC-ACIDS; ALCOHOLS; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE
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 {[}13-03-00674]; Ural Branch of the Russian Academy of Sciences {[}15-21-3-5]; State Program for Supporting of Leading Scientific School of the Russian Federation {[}NSh 3656.2014.3]
Funding-Text	The work was financially supported by the Russian Foundation for Basic Research (grant 13-03-00674), the Ural Branch of the Russian Academy of Sciences (project no. 15-21-3-5) and the State Program for Supporting of Leading Scientific School of the Russian Federation (grant NSh 3656.2014.3).
Number-of-Cited-References	42
Usage-Count-Since-2013	23
Journal-ISO	Tetrahedron-Asymmetry
Doc-Delivery-Number	CF6MU