Spiroanthraceneoxazolidine as a synthetic equivalent of methanimine in the reaction with donor-acceptor cyclopropanes. Synthesis of diethyl 5-arylpyrrolidine-3,3-dicarboxylates / Buev Evgeny M.,Moshkin Vladimir S.,Sosnovskikh Vyacheslav Y. // TETRAHEDRON LETTERS. - 2016. - V. 57, l. 33. - P. 3731-3734.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Spiroanthraceneoxazolidine reacts with diethyl 2-arylcyclopropane-1,1-dicarboxylates at 140-200 degrees C in the presence of magnesium bromide diethyl etherate to give 5-arylpyrrolidine-3,3-dicarboxylates. Yield and ease of the reaction were well correlated with the electron-donating nature of the aryl(heteroaryl) substituent at the cyclopropane ring. This one-pot domino reaction allows the formation of a number of functionalized arylpyrrolidines in 16-54\% yields. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

Spiroanthraceneoxazolidine; Donor-acceptor cyclopropanes; {[}3+2] Annulation; Arylpyrrolidines AROMATIC AZOMETHINE IMINES; 3+2 DIPOLAR CYCLOADDITION; FLASH VACUUM THERMOLYSIS; ONE-POT SYNTHESIS; YLIDES; 5-ARYLOXAZOLIDINES; REARRANGEMENT; PYRROLIDINES; OXAZOLIDINES; DERIVATIVES

DOI:

10.1016/j.tetlet.2016.07.007

Web of Science ID:

ISI:000381536700012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 17
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	AROMATIC AZOMETHINE IMINES; 3+2 DIPOLAR CYCLOADDITION; FLASH VACUUM THERMOLYSIS; ONE-POT SYNTHESIS; YLIDES; 5-ARYLOXAZOLIDINES; REARRANGEMENT; PYRROLIDINES; OXAZOLIDINES; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	mvslc@mail.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	Russian Science Foundation {[}14-13-00388]
Funding-Text	This work was financially supported by the Russian Science Foundation (Grant 14-13-00388).
Number-of-Cited-References	57
Usage-Count-Last-180-days	6
Usage-Count-Since-2013	16
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	DT5QC