Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions

Ichiro Hayakawa; Yuji Yamanaka; Koichi Mitsudo; Hiromi Ota; Akira Sakakura

doi:10.3987/COM-17-13820

Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions

Ichiro Hayakawa, Yuji Yamanaka, Koichi Mitsudo, Hiromi Ota, Akira Sakakura

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

Abstract

The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.

Original language	English
Pages (from-to)	2299-2306
Number of pages	8
Journal	Heterocycles
Volume	94
Issue number	12
DOIs	https://doi.org/10.3987/COM-17-13820
Publication status	Published - 2017

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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@article{268fe9db3e4a4adeb1e7bf78fe36ce34,

title = "Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions",

abstract = "The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.",

author = "Ichiro Hayakawa and Yuji Yamanaka and Koichi Mitsudo and Hiromi Ota and Akira Sakakura",

note = "Funding Information: We are grateful to Professor Hideo Kigoshi (University of Tsukuba) and Professor Seiji Suga (Okayama University) for their interest in this work. This work was supported by a Grants-in-Aid for Scientific Research (C) (Grant Number JP17K01949) from the Japan Society for the Promotion of Science (JSPS). I.H. thanks the Okayama Foundation for Science and Technology for financial support. The authors thank the Division of Instrumental Analysis, Okayama University for the NMR and HR-ESIMS measurements. Publisher Copyright: {\textcopyright} 2017 The Japan Institute of Heterocyclic Chemistry.",

year = "2017",

doi = "10.3987/COM-17-13820",

language = "English",

volume = "94",

pages = "2299--2306",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

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T1 - Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions

AU - Hayakawa, Ichiro

AU - Yamanaka, Yuji

AU - Mitsudo, Koichi

AU - Ota, Hiromi

AU - Sakakura, Akira

N1 - Funding Information: We are grateful to Professor Hideo Kigoshi (University of Tsukuba) and Professor Seiji Suga (Okayama University) for their interest in this work. This work was supported by a Grants-in-Aid for Scientific Research (C) (Grant Number JP17K01949) from the Japan Society for the Promotion of Science (JSPS). I.H. thanks the Okayama Foundation for Science and Technology for financial support. The authors thank the Division of Instrumental Analysis, Okayama University for the NMR and HR-ESIMS measurements. Publisher Copyright: © 2017 The Japan Institute of Heterocyclic Chemistry.

PY - 2017

Y1 - 2017

N2 - The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.

AB - The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.

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SN - 0385-5414

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Regioselective dmad-insertion reaction of silyl dienol ether of γ-pyrone under catalyst- and heating-free conditions

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