Issue 96, 2012
From the journal:

Chemical Communications

Lewis acid-catalyzed unexpected selective C–C bond cleavage: an efficient and mild construction of cyclopentenes†

Qiong Yua  and  Shengming Ma*ab  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China
E-mail: masm@sioc.ac.cn
Fax: +86-21-6260-9305

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China

Abstract

An intriguing Lewis acid-catalyzed intramolecular ring-opening/cyclization reaction of cyclopropylvinylallenes is developed. This process proceeds at ambient temperature to afford the structurally diverse cyclopentenes exclusively, which demonstrates the unique reactivity of 1,3,4-alkatrien-2-yl cyclopropanes.

Graphical abstract: Lewis acid-catalyzed unexpected selective C–C bond cleavage: an efficient and mild construction of cyclopentenes

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Article information

DOI
https://doi.org/10.1039/C2CC36672J
Article type
Communication
Submitted
13 Sep 2012
Accepted
14 Oct 2012
First published
15 Oct 2012

Chem. Commun., 2012,48, 11784-11786

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Lewis acid-catalyzed unexpected selective C–C bond cleavage: an efficient and mild construction of cyclopentenes

Q. Yu and S. Ma, Chem. Commun., 2012, 48, 11784 DOI: 10.1039/C2CC36672J

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