Direct diastereoselective addition of l-menthol to activated 1,2,4-triazin-5(4H)-one / Chupakhin ON,Zyryanov GV,Rusinov VL,Krasnov VP,Levit GL,Korolyova MA,Kodess MI // TETRAHEDRON LETTERS. - 2001. - V. 42, l. 12. - P. 2393-2395.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

For the first time in a triazine series it has been found that addition of a chiral O-nucleophile. l-menthol, to the C-6-unsubstituted atom of 3-phenyl-1,2,4-triazin-5(4H)-one 1 activated by aliphatic acid anhydrides proceeds diastereoselectively to form a mixture of 1-acyl-6-{[}(1 `R,3'R,4'S)-menthyl-3')]-3-phenyl-(6S)-1,6-dihydro-1,2,4-triazin-5(4H)-o nes 2 and 1-acyl-6-{[}(1'R,3'R, 4'S)-menthyl-3')]-3-phenyl-(6R)-1,6-dihydro-1,2,4-triazin-5(4H)-ones 3 in which the diastereomers 2 predominate. The diastereoselectivity of the process improves as the size of the N-1-acyl substituent increases. (C) 2001 Published by Elsevier Science Ltd.

Author keywords:

CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS; ENANTIOPURE N-ACYLDIHYDROPYRIDONES; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES

DOI:

10.1016/S0040-4039(01)00154-X

Web of Science ID:

ISI:000167535400039

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR 18
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS; ENANTIOPURE N-ACYLDIHYDROPYRIDONES; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Number-of-Cited-References	16
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	1
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	412CA