The Diels-Alder reaction using a vinyl sulfoxide activated by the participation of a neighboring epoxide group

Hitoshi Abe; Daisuke Tsuchida; Setsuo Kashino; Yasuo Takeuchi; Takashi Harayama

doi:10.1248/cpb.47.833

The Diels-Alder reaction using a vinyl sulfoxide activated by the participation of a neighboring epoxide group

Hitoshi Abe, Daisuke Tsuchida, Setsuo Kashino, Yasuo Takeuchi, Takashi Harayama

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

A vinyl sulfoxide, which is considered to be a moderately reactive dienophile, could be activated by neighboring participation of an epoxide group. The Diels-Alder reaction of ortho-epoxyphenyl vinyl sulfoxide with cyclopentadiene in the presence of Yb(OTf)₃ proceeded smoothly even at room temperature to afford the epoxy-opened cycloadducts with moderate stereoselectivity.

Original language	English
Pages (from-to)	833-837
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	47
Issue number	6
DOIs	https://doi.org/10.1248/cpb.47.833
Publication status	Published - Jun 1999

Keywords

Diels-Alder reaction
Epoxide
Neighboring participation
Sulfonium salt
Vinyl sulfoxide

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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abstract = "A vinyl sulfoxide, which is considered to be a moderately reactive dienophile, could be activated by neighboring participation of an epoxide group. The Diels-Alder reaction of ortho-epoxyphenyl vinyl sulfoxide with cyclopentadiene in the presence of Yb(OTf)3 proceeded smoothly even at room temperature to afford the epoxy-opened cycloadducts with moderate stereoselectivity.",

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AU - Abe, Hitoshi

AU - Tsuchida, Daisuke

AU - Kashino, Setsuo

AU - Takeuchi, Yasuo

AU - Harayama, Takashi

PY - 1999/6

Y1 - 1999/6

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AB - A vinyl sulfoxide, which is considered to be a moderately reactive dienophile, could be activated by neighboring participation of an epoxide group. The Diels-Alder reaction of ortho-epoxyphenyl vinyl sulfoxide with cyclopentadiene in the presence of Yb(OTf)3 proceeded smoothly even at room temperature to afford the epoxy-opened cycloadducts with moderate stereoselectivity.

KW - Diels-Alder reaction

KW - Epoxide

KW - Neighboring participation

KW - Sulfonium salt

KW - Vinyl sulfoxide

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The Diels-Alder reaction using a vinyl sulfoxide activated by the participation of a neighboring epoxide group

Abstract

Keywords

ASJC Scopus subject areas

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