Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes

Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes

Author Ali, Bakhat Google Scholar
Zukerman-Schpector, Julio Google Scholar
Ferreira, Fernando P. Autor UNIFESP Google Scholar
Shamim, Anwar Google Scholar
Pimenta, Daniel C. Google Scholar
Stefani, Helici A. Google Scholar
Institution Universidade de São Paulo (USP)
Universidade Federal de São Carlos (UFSCar)
Universidade Federal de São Paulo (UNIFESP)
Inst Butantan
Abstract The cyclodimerization reaction of N-substituted-5-hydroxy-pyrrolydinones promoted by BF3 center dot Et2O and HCl to obtain symmetrical 1,4-dioxane derivatives was achieved in moderate to good yields, mild conditions, and short reaction times. These transformations render a promising alternative route that provides access to diverse 1,4-dioxane derivatives with a wide structural diversity. (C) 2015 Elsevier B.V. All rights reserved.
Keywords Amines
N-Acyliminium
Acid catalysis
Cyclodimerization
1,4-Dioxane
Language English
Sponsor Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
FINEP
Grant number FAPESP: 2012/00424-2
FAPESP: 2011/11499-0
FAPESP: -2012/17954-4
CNPq: 308.320/2010-7
CNPq: 305626/2013-2
FINEP: 01.09.0278.04
Date 2015-02-25
Published in Tetrahedron Letters. Oxford: Pergamon-Elsevier B.V., v. 56, n. 9, p. 1153-1158, 2015.
ISSN 0040-4039 (Sherpa/Romeo, impact factor)
Publisher Elsevier B.V.
Extent 1153-1158
Origin http://dx.doi.org/10.1016/j.tetlet.2015.01.059
Access rights Closed access
Type Article
Web of Science ID WOS:000350087800027
URI http://repositorio.unifesp.br/handle/11600/38774

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