Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Tosyl-(S)-Prolyl Chloride and its Structural Analogs / Vakarov S. A.,Gruzdev D. A.,Chulakov E. N.,Sadretdinova L. Sh.,Ezhikova M. A.,Kodess M. I.,Levit G. L.,Krasnov V. P. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2014. - V. 50, l. 6. - P. 838-855.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.

Author keywords:

acyl chlorides; proline; racemic amines; acylation; diastereoselectivity; kinetic resolution N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; KINETIC RESOLUTION; ACID-DERIVATIVES; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; 3-N,N-DIACYLAMINOQUINAZOLIN-4(3H)-ONES; (+/-)-2-METHYLINDOLINE; REAGENT; LIPASE

DOI:

10.1007/s10593-014-1538-8

Web of Science ID:

ISI:000340878300006

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	SEP
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	N-PHTHALOYL-(S)-AMINO ACYL CHLORIDES; KINETIC RESOLUTION; ACID-DERIVATIVES; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; 3-N,N-DIACYLAMINOQUINAZOLIN-4(3H)-ONES; (+/-)-2-METHYLINDOLINE; REAGENT; LIPASE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	gruzdev-da@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}13-03-00674, 13-03-12188]; 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 13-03-00674, 13-03-12188), 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	39
Usage-Count-Since-2013	12
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	AN8TV