Issue 24, 2009
From the journal:

Chemical Communications

Furansversus 4H-pyrans: catalyst-controlled regiodivergent tandem Michael addition–cyclization reaction of 2-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds†

Yuanjing Xiaoa  and  Junliang Zhang*ab  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N, Zhongshan Road, Shanghai 200062, P. R. China
E-mail: jlzhang@chem.ecnu.edu.cn
Fax: (+86) 21-6223-5039

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China

Abstract

The DBU-catalyzed reaction of 1-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds produces 4H-pyrans in moderate to excellent yield, whereas the cationic Pd(II)-catalyzed reaction affords furans regioselectively.

Graphical abstract: Furans versus 4H-pyrans: catalyst-controlled regiodivergent tandem Michael addition–cyclization reaction of 2-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds

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Article information

DOI
https://doi.org/10.1039/B905267D
Article type
Communication
Submitted
16 Mar 2009
Accepted
15 Apr 2009
First published
11 May 2009

Chem. Commun., 2009, 3594-3596

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Furans versus 4H-pyrans: catalyst-controlled regiodivergent tandem Michael addition–cyclization reaction of 2-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds

Y. Xiao and J. Zhang, Chem. Commun., 2009, 3594 DOI: 10.1039/B905267D

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