Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

Yuya Yamasaki; Takaaki Kumagai; Shota Kanno; Fumitoshi Kakiuchi; Takuya Kochi

doi:10.1021/acs.joc.8b01288

Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

Yuya Yamasaki, Takaaki Kumagai, Shota Kanno, Fumitoshi Kakiuchi, Takuya Kochi

Department of Chemistry

Research output: Contribution to journal › Article

7 Citations (Scopus)

Abstract

Selective long-distance isomerization of terminal alkenes to silyl enol ethers proceeded via nondissociative chain walking using phenanthroline palladium catalysts. Notable features achieved taking advantage of the nondissociative chain walking mechanism include high efficiency obtained regardless of the chain length, high chemoselectivity toward terminal alkenes over internal ones, and retention of the stereoconfiguration of the stereocenter on the alkyl chain.

Original language	English
Pages (from-to)	9322-9333
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	83
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.8b01288
Publication status	Published - 2018 Aug 17

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ASJC Scopus subject areas

Organic Chemistry

Cite this

Yamasaki, Y., Kumagai, T., Kanno, S., Kakiuchi, F., & Kochi, T. (2018). Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking. Journal of Organic Chemistry, 83(16), 9322-9333. https://doi.org/10.1021/acs.joc.8b01288

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10.1021/acs.joc.8b01288