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Preparation of a Cycloheptane Ring from a 1,2-Diketone with High Stereoselectivity

Yoshiaki Takada, Kenichi Nomura and Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-Katsura, Nishikyo, Kyoto 615-8510, Japan, Email: matsubarorgrxn.mbox.media.kyoto-u.ac.jp

Y. Takada, K. Nomura, S. Matubara, Org. Lett., 2010, 12, 5204-5205.

DOI: 10.1021/ol102237b (free Supporting Information)


Abstract

Treatment of 1,6-dialkylhexa-1,5-diene-3,4-diones with bis(iodozincio)methane gave zinc alkoxides of cis-5,6-dialkylcyclohepta-3,7-diene-1,3-diol in good yields at room temperature via a cis-divinylcyclopropane-1,2-diol and a subsequent Cope rearrangement. The reaction proceeded with high stereospecificity.

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Key Words

cycloheptanones, Cope rearrangement


ID: J54-Y2010-3220