Issue 1, 2015
From the journal:

Organic & Biomolecular Chemistry

Preparation of cycloheptane ring by nucleophilic cyclopropanation of 1,2-diketones with bis(iodozincio)methane†

Ryosuke Haraguchi,a   Yoshiaki Takadaa  and  Seijiro Matsubara*a  

* Corresponding authors

a Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
E-mail: matsubara.seijiro.2e@kyoto-u.ac.jp
Fax: +81(75)3832438

Abstract

The nucleophilic cyclopropanation of hexa-1,5-diene-3,4-diones with bis(iodozincio)methane afforded the Zn alkoxides of cis-dialkenylcyclopropane-1,2-diols stereoselectively. The subsequent oxy-Cope rearrangement afforded the corresponding Zn alkoxides of 5,6-dialkylcyclohepta-3,7-diene-1,3-diols.

Graphical abstract: Preparation of cycloheptane ring by nucleophilic cyclopropanation of 1,2-diketones with bis(iodozincio)methane

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Article information

DOI
https://doi.org/10.1039/C4OB01474J
Article type
Paper
Submitted
14 Jul 2014
Accepted
20 Oct 2014
First published
20 Oct 2014

Org. Biomol. Chem., 2015,13, 241-247

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Preparation of cycloheptane ring by nucleophilic cyclopropanation of 1,2-diketones with bis(iodozincio)methane

R. Haraguchi, Y. Takada and S. Matsubara, Org. Biomol. Chem., 2015, 13, 241 DOI: 10.1039/C4OB01474J

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