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

Organic & Biomolecular Chemistry Pub Date: 2014-10-20 DOI: 10.1039/C4OB01474J

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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