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Org Lett. 2015 Dec 04;17(23):5843-5. doi: 10.1021/acs.orglett.5b03065. Epub 2015 Nov 19.

Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones.

Organic letters

Kazuhiro Okamoto, Takuya Shimbayashi, Eisuke Tamura, Kouichi Ohe

Affiliations

  1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University , Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

PMID: 26584237 DOI: 10.1021/acs.orglett.5b03065

Abstract

We have developed an indium-catalyzed [2 + 2] cycloaddition of allylsilanes to alkynones leading to selective cyclobutenone formation. The resulting cyclobutenones were readily converted to the oxidized products by Tamao-Fleming oxidation or the ring-opened products by an electrocyclic reaction.

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