Nucleophilic properties of a nonstabilized azomethine ylide derived from sarcosine and cyclohexanone. A novel domino reaction leading to substituted 4-aryl-2-pyrrolidones / Moshkin Vladimir S.,Sosnovskikh Vyacheslav Ya.,Roeschenthaler Gerd-Volker // TETRAHEDRON LETTERS. - 2012. - V. 53, l. 28. - P. 3568-3572.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

A nonstabilized asymmetric azomethine ylide derived from sarcosine and cyclohexanone reacts with 3-substituted coumarins and ethyl benzylidene malonate to give 4-aryl-2-pyrrolidones in moderate yields, and the adducts of classical 1,3-dipolar cycloadditions as the minor products. The main reaction proceeds via a domino process, starting with 1,4-nucleophilic addition to the conjugated double bond, and represents the first example of the nucleophilic properties of a nonstabilized azomethine ylide. (C) 2012 Elsevier Ltd. All rights reserved.

Author keywords:

Nonstabilized asymmetric azomethine ylide; Domino reaction; 4-Aryl-2-pyrrolidones; 1,4-Nucleophilic addition; 3-Substituted coumarins; {[}3+2] Cycloaddition ALPHA-AMINO-ACIDS; DECARBOXYLATIVE TRANSAMINATION; ROUTE; MECHANISM

DOI:

10.1016/j.tetlet.2012.05.008

Web of Science ID:

ISI:000305856100007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 11
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ALPHA-AMINO-ACIDS; DECARBOXYLATIVE TRANSAMINATION; ROUTE; MECHANISM
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	mvslc@mail.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	DFG {[}RO 362/50/1]
Funding-Text	This work was supported financially by the DFG RO 362/50/1.
Number-of-Cited-References	30
Usage-Count-Since-2013	8
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	966RW