Novel sequential 1,4-Brook rearrangement-Wittig reaction: New one-pot approach for silyl dienol ethers

Yuji Matsuya; Azusa Koiwai; Daishiro Minato; Kenji Sugimoto; Naoki Toyooka

doi:10.1016/j.tetlet.2012.08.114

Novel sequential 1,4-Brook rearrangement-Wittig reaction: New one-pot approach for silyl dienol ethers

Yuji Matsuya^*, Azusa Koiwai, Daishiro Minato, Kenji Sugimoto, Naoki Toyooka

^*Corresponding author for this work

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

15 Scopus citations

Abstract

A novel one-pot synthetic method of silyl dienol ethers via 1,4-Brook rearrangement-Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.

Original language	English
Pages (from-to)	5955-5957
Number of pages	3
Journal	Tetrahedron Letters
Volume	53
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2012.08.114
State	Published - 2012/10/31

Keywords

1,4-Brook rearrangement
Silyl dienol ether
Tandem reaction
Wittig reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Novel sequential 1,4-Brook rearrangement-Wittig reaction: New one-pot approach for silyl dienol ethers",

abstract = "A novel one-pot synthetic method of silyl dienol ethers via 1,4-Brook rearrangement-Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.",

keywords = "1,4-Brook rearrangement, Silyl dienol ether, Tandem reaction, Wittig reaction",

author = "Yuji Matsuya and Azusa Koiwai and Daishiro Minato and Kenji Sugimoto and Naoki Toyooka",

note = "Funding Information: This work was supported in part by a Grant-in-Aid (No. 24790008) for Scientific Research by the Ministry of Education, Culture, Sports, Science, and Technology of the Japanese Government. ",

year = "2012",

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doi = "10.1016/j.tetlet.2012.08.114",

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T1 - Novel sequential 1,4-Brook rearrangement-Wittig reaction

T2 - New one-pot approach for silyl dienol ethers

AU - Matsuya, Yuji

AU - Koiwai, Azusa

AU - Minato, Daishiro

AU - Sugimoto, Kenji

AU - Toyooka, Naoki

N1 - Funding Information: This work was supported in part by a Grant-in-Aid (No. 24790008) for Scientific Research by the Ministry of Education, Culture, Sports, Science, and Technology of the Japanese Government.

PY - 2012/10/31

Y1 - 2012/10/31

N2 - A novel one-pot synthetic method of silyl dienol ethers via 1,4-Brook rearrangement-Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.

AB - A novel one-pot synthetic method of silyl dienol ethers via 1,4-Brook rearrangement-Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.

KW - 1,4-Brook rearrangement

KW - Silyl dienol ether

KW - Tandem reaction

KW - Wittig reaction

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DO - 10.1016/j.tetlet.2012.08.114

M3 - 学術論文

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SN - 0040-4039

VL - 53

SP - 5955

EP - 5957

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Novel sequential 1,4-Brook rearrangement-Wittig reaction: New one-pot approach for silyl dienol ethers

Abstract

Keywords

ASJC Scopus subject areas

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