Issue 22, 2010
From the journal:

Organic & Biomolecular Chemistry

Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans†

Xiuzhao Yu,a   Zhongyan Caoa  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,

Abstract

Highly substituted 4H-pyrans can be smoothly synthesized from readily available 2-(1-alkynyl)-2-alkene-1-ones by DBU- or n-Bu3P catalyzed hetero-[4+2] cycloaddition reactions, in which 2-(1-alkynyl)-2-alkene-1-ones act as both heterodiene and heterodinenophile.

Graphical abstract: Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans

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Article information

DOI
https://doi.org/10.1039/C0OB00334D
Article type
Communication
Submitted
28 Jun 2010
Accepted
08 Sep 2010
First published
27 Sep 2010

Org. Biomol. Chem., 2010,8, 5059-5061

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Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans

X. Yu, Z. Cao and J. Zhang, Org. Biomol. Chem., 2010, 8, 5059 DOI: 10.1039/C0OB00334D

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