Uncatalyzed, highly stereoselective addition of alpha-morpholinostyrene to 3-nitro-2-(trihalomethyl)-2H-chromenes. Synthesis of trans cis- and trans-trans-3-nitro-4-phenacyl-(2-trihalomethyl)chromanes / Korotaev Vladislav Yu,Kotovich Ivan V.,Barkov Alexey Yu,Kutyashev Igor B.,Kodess Mikhail I.,Sosnovskikh Vyacheslav Ya // TETRAHEDRON. - 2016. - V. 72, l. 1. - P. 216-226.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Reactions of 2-R-3-nitro-2H-chromenes (R=CF3, CCl3, Ph) with alpha-morpholinostyrene in acetonitrile proceed diastereoselectively to give mainly trans cis-2,3,4-trisubstituted chromane enamines at room temperature and trans trans-chromane enamines at 60 degrees C as a result of nucleophilic addition at the C-4 atom of the chromene system. Acid hydrolysis of these compounds proceeded with retention of the configuration of the pyran ring and gave 4-phenacylchromanes. The stereochemistry of the products was established by X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2H-chromenes; alpha-Morpholinostyrene; Chromanes; Stereoselectivity CASCADE REACTION; ENAMINES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; DERIVATIVES; CYCLOADDITION; NUCLEOPHILES; TAUTOMERISM; CHROMANES

DOI:

10.1016/j.tet.2015.11.036

Web of Science ID:

ISI:000367276300024

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 7
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	CASCADE REACTION; ENAMINES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; DERIVATIVES; CYCLOADDITION; NUCLEOPHILES; TAUTOMERISM; CHROMANES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-00179]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grant 14-03-00179) and performed within the State Task from the Ministry of Education and Science of Russian Federation.
Number-of-Cited-References	27
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	10
Journal-ISO	Tetrahedron
Doc-Delivery-Number	CZ7JS