Highly diastereoselective synthesis of novel 2,3,4-trisubstituted chromanes via the reaction of 3-nitro-2-(trihalomethyl)- and 3-nitro-2-phenyl-2H-chromenes with 1-morpholinocyclopentene / Korotaev Vladislav Y.,Kutyashev Igor B.,Barkov Alexey Y.,Sosnovskikh Vyacheslav Y. // TETRAHEDRON. - 2017. - V. 73, l. 34. - P. 5122-5137.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

The reaction of 3-nitro-2-trifluoro(trichloro)methyl- and 3-nitro-2-phenyl-2H-chromenes with 1-morpholinocyclopentene under the conditions of kinetic or thermodynamic control led to the formation of products due to enamine addition at the C-4 atom of chromene as individual cis,trans- or trans,trans-isomers, differing by the position of double bond in the enamine moiety. Hydrolysis of these compounds in dilute HCI did not cause changes of pyran ring configuration and provided the respective 4-(cyclopentanon-2-yl)chromanes with anti-configuration of hydrogen atoms at the C-4 and C-2' atoms. Stereochemistry of the obtained compounds was confirmed by X-ray structural analysis. (C) 2017 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2H-chromenes; 1-Morpholinocyclopentene; Chromanes; Stereoselectivity STEREOSELECTIVE ADDITION; ALPHA-NITROALKENES; MICHAEL ADDITION; NITRONIC ESTERS; N-OXIDES; ENAMINES; 3-NITRO-2H-CHROMENES; STEREOCHEMISTRY; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; CYCLOALKANONES.

DOI:

10.1016/j.tet.2017.07.003

Web of Science ID:

ISI:000407536500009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 24
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	STEREOSELECTIVE ADDITION; ALPHA-NITROALKENES; MICHAEL ADDITION; NITRONIC ESTERS; N-OXIDES; ENAMINES; 3-NITRO-2H-CHROMENES; STEREOCHEMISTRY; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; CYCLOALKANONES.
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	korotaev.vladislav@urfu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Number-of-Cited-References	26
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	1
Journal-ISO	Tetrahedron
Doc-Delivery-Number	FD4XW