Synthesis of beta-(trifluoromethyl)furans and spiro-gem-dichlorocyclopropanes from cyclic 1,3-dicarbonyl compounds and alpha-(trihaloethylidene)nitroethanes / Barkov Alexey Yu.,Korotaev Vladislav Yu.,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON LETTERS. - 2013. - V. 54, l. 32. - P. 4181-4184.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

While 1,3-dicarbonyl compounds react with (E)-1,1,1-trifluoro-3-nitrobut-2-ene in the presence of sodium acetate to produce the target beta-(trifluoromethyl)furans, their reaction with (E)-1,1,1-trichloro-3-nitrobut-2-ene, under the same conditions, took an entirely different course and gave spiro-gem-dichlorocyclopropanes bearing a 1-nitroethyl moiety, with high diastereoselectivity and in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

beta-(Trifluoromethyl)furans; alpha-(Trihaloethylidene)nitroethanes; 1,3-Dicarbonyl compounds; Michael addition; Spiro-cyclopropanation ORGANIC FLUORINE-COMPOUNDS; ONE-POT SYNTHESIS; STEREOSELECTIVE CONSTRUCTION; MICHAEL ADDITION; NITRO-OLEFINS; DERIVATIVES; CYCLOHEXANE-1,3-DIONES; NITROALKENES; HETEROCYCLES; 3,3,3-TRICHLORO(TRIFLUORO)-1-NITROPROPENES

DOI:

10.1016/j.tetlet.2013.05.129

Web of Science ID:

ISI:000321802800012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 7
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ORGANIC FLUORINE-COMPOUNDS; ONE-POT SYNTHESIS; STEREOSELECTIVE CONSTRUCTION; MICHAEL ADDITION; NITRO-OLEFINS; DERIVATIVES; CYCLOHEXANE-1,3-DIONES; NITROALKENES; HETEROCYCLES; 3,3,3-TRICHLORO(TRIFLUORO)-1-NITROPROPENES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}11-03-00126]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grant 11-03-00126).
Number-of-Cited-References	60
Usage-Count-Since-2013	10
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	183GP