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

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

Research output: Contribution to journalArticle

4 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 languageEnglish
Pages (from-to)9322-9333
Number of pages12
JournalJournal of Organic Chemistry
Volume83
Issue number16
DOIs
Publication statusPublished - 2018 Aug 17

Fingerprint

Alkenes
Isomerization
Phenanthrolines
Ethers
Palladium
Chain length
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking. / Yamasaki, Yuya; Kumagai, Takaaki; Kanno, Shota; Kakiuchi, Fumitoshi; Kochi, Takuya.

In: Journal of Organic Chemistry, Vol. 83, No. 16, 17.08.2018, p. 9322-9333.

Research output: Contribution to journalArticle

@article{09a7ebfae4b842ef93b805d62e3cba58,
title = "Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking",
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.",
author = "Yuya Yamasaki and Takaaki Kumagai and Shota Kanno and Fumitoshi Kakiuchi and Takuya Kochi",
year = "2018",
month = "8",
day = "17",
doi = "10.1021/acs.joc.8b01288",
language = "English",
volume = "83",
pages = "9322--9333",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking

AU - Yamasaki, Yuya

AU - Kumagai, Takaaki

AU - Kanno, Shota

AU - Kakiuchi, Fumitoshi

AU - Kochi, Takuya

PY - 2018/8/17

Y1 - 2018/8/17

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85050356658&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85050356658&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b01288

DO - 10.1021/acs.joc.8b01288

M3 - Article

VL - 83

SP - 9322

EP - 9333

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 16

ER -