Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

Hirokazu Tsukamoto; Kazuya Ito; Takayuki Doi

doi:10.1039/c8cc02589d

Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

Hirokazu Tsukamoto, Kazuya Ito, Takayuki Doi

PHA - Molecular Pharmaceutical Science

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

10 Citations (Scopus)

Abstract

Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.

Original language	English
Pages (from-to)	5102-5105
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	40
DOIs	https://doi.org/10.1039/c8cc02589d
Publication status	Published - 2018

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles",

abstract = "Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.",

author = "Hirokazu Tsukamoto and Kazuya Ito and Takayuki Doi",

note = "Funding Information: This work was partly supported by JSPS KAKENHI Grant Number JP15K07849, the Research Foundation for Pharmaceutical Sciences, Suntory Foundation for Life Sciences and the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP18am0101095 and JP18am0101100. Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

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T1 - Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

AU - Tsukamoto, Hirokazu

AU - Ito, Kazuya

AU - Doi, Takayuki

N1 - Funding Information: This work was partly supported by JSPS KAKENHI Grant Number JP15K07849, the Research Foundation for Pharmaceutical Sciences, Suntory Foundation for Life Sciences and the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP18am0101095 and JP18am0101100. Publisher Copyright: © 2018 The Royal Society of Chemistry.

PY - 2018

Y1 - 2018

N2 - Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.

AB - Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.

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JO - Chemical Communications

JF - Chemical Communications

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Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

Abstract

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