Issue 46, 2010
From the journal:

Chemical Communications

An unprecedented stereoselective [2+2] cycloreversion of cyclobutanones†

Xiufang Ji,a   Quanrui Wang*a  and  Andreas Goeke*b  

* Corresponding authors

a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China
E-mail: qrwang@fudan.edu.cn
Fax: (+86)(21) 65641740
Tel: (+86)(21) 65643978

b Givaudan Fragrances (Shanghai) Ltd., 298 Li Shi Zhen Road, Shanghai 201203, China
E-mail: andreas.goeke@givaudan.com

Abstract

A one-pot metathetic ring opening of substituted bicyclo[3.2.0]heptenones to linear polyene ketones is described. The reaction proceeds with conservation of the endocyclic (Z)-double bond. Exo-substituted vinylcyclobutanones result in (4Z,6E)-configured trienones, while endo-substituted phenyl derivatives generate (4Z,6Z)-configured dienones.

Graphical abstract: An unprecedented stereoselective [2+2] cycloreversion of cyclobutanones

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Article information

DOI
https://doi.org/10.1039/C0CC02694H
Article type
Communication
Submitted
21 Jul 2010
Accepted
23 Sep 2010
First published
20 Oct 2010

Chem. Commun., 2010,46, 8845-8847

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An unprecedented stereoselective [2+2] cycloreversion of cyclobutanones

X. Ji, Q. Wang and A. Goeke, Chem. Commun., 2010, 46, 8845 DOI: 10.1039/C0CC02694H

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