Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro{[}indoline-3,2'-pyrrolidin]2-ones and spiro{[}indoline-3,3'-pyrrolizin]-2-ones / Barkov Alexey Yu.,Zimnitskiy Nikolay S.,Korotaev Vladislav Yu.,Kutyashev Igor B.,Moshkin Vladimir S.,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON. - 2016. - V. 72, l. 43. - P. 6825-6836.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Reactions of 3,3,3-trihalogen-1-nitropropenes with N-alkyl-alpha-amino acids (sarcosine, proline) and isatins proceed regio- and diastereoselectively to give a wide range of trihalomethylated spiro{[}indoline-3,2'pyrrolidin]-2-ones and spiro{[}indoline-3,3'-pyrrolizin]-2-ones in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate stabilised azomethine ylide at the double bond of the nitroalkenes. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

3,3,3-Trihalogeno-1-nitropropenes; Stabilised azomethine ylides; 1,3-Dipolar cycloaddition; Spirooxindoles ALPHA-AMINO-ACIDS; NATURAL-PRODUCTS; REGIOSELECTIVE SYNTHESIS; DECARBOXYLATIVE ROUTE; ORGANIC-SYNTHESIS; DERIVATIVES; 3,3,3-TRICHLORO(TRIFLUORO)-1-NITROPROPENES; 1,1,1-TRICHLORO-3-NITROPROPENE; 2-MORPHOLINOALK-1-ENES; SPIROOXINDOLES

DOI:

10.1016/j.tet.2016.09.017

Web of Science ID:

ISI:000385322800008

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT 27
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ALPHA-AMINO-ACIDS; NATURAL-PRODUCTS; REGIOSELECTIVE SYNTHESIS; DECARBOXYLATIVE ROUTE; ORGANIC-SYNTHESIS; DERIVATIVES; 3,3,3-TRICHLORO(TRIFLUORO)-1-NITROPROPENES; 1,1,1-TRICHLORO-3-NITROPROPENE; 2-MORPHOLINOALK-1-ENES; SPIROOXINDOLES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017 Zimnitskiy, Nikolay/H-1666-2016 Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Zimnitskiy, Nikolay/0000-0002-1156-0922 Korotaev, Vladislav/0000-0002-7492-5116
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	63
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	14
Journal-ISO	Tetrahedron
Doc-Delivery-Number	DY7PX