Synthesis of Rigid Macrocyclic Phenols and Their Catalytic Applications in Diels-Alder Reactions

Tomoya Hayashi; Yuki Ohishi; Junya Chiba; Masahiko Inouye

doi:10.1002/ejoc.202200136

Synthesis of Rigid Macrocyclic Phenols and Their Catalytic Applications in Diels-Alder Reactions

Tomoya Hayashi, Yuki Ohishi^*, Junya Chiba, Masahiko Inouye^*

^*Corresponding author for this work

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

Abstract

Macrocyclic catalysts having a phenol-acetylene-phenol triad were developed as a hydrogen-bond donor catalyst. The rigid macrocyclic framework suppressed intramolecular hydrogen bonds between neighboring phenolic hydroxy groups. The preorganized phenol-acetylene-phenol moiety formed efficient intermolecular hydrogen bonds with carbonyl groups of substrates. The hydrogen-bond donor catalysts accelerated the Diels-Alder reaction of methyl vinyl ketone with cyclopentadiene. The catalytic ability was higher than that of an acyclic counterpart.

Original language	English
Article number	e202200136
Journal	European Journal of Organic Chemistry
Volume	2022
Issue number	32
DOIs	https://doi.org/10.1002/ejoc.202200136
State	Published - 2022/08/26

Keywords

Diels-Alder reactions
Host-guest systems
Hydrogen-bond donor catalysts
Macrocycles
Phenols

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.202200136

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title = "Synthesis of Rigid Macrocyclic Phenols and Their Catalytic Applications in Diels-Alder Reactions",

abstract = "Macrocyclic catalysts having a phenol-acetylene-phenol triad were developed as a hydrogen-bond donor catalyst. The rigid macrocyclic framework suppressed intramolecular hydrogen bonds between neighboring phenolic hydroxy groups. The preorganized phenol-acetylene-phenol moiety formed efficient intermolecular hydrogen bonds with carbonyl groups of substrates. The hydrogen-bond donor catalysts accelerated the Diels-Alder reaction of methyl vinyl ketone with cyclopentadiene. The catalytic ability was higher than that of an acyclic counterpart.",

keywords = "Diels-Alder reactions, Host-guest systems, Hydrogen-bond donor catalysts, Macrocycles, Phenols",

author = "Tomoya Hayashi and Yuki Ohishi and Junya Chiba and Masahiko Inouye",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = aug,

day = "26",

doi = "10.1002/ejoc.202200136",

language = "英語",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "32",

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TY - JOUR

T1 - Synthesis of Rigid Macrocyclic Phenols and Their Catalytic Applications in Diels-Alder Reactions

AU - Hayashi, Tomoya

AU - Ohishi, Yuki

AU - Chiba, Junya

AU - Inouye, Masahiko

PY - 2022/8/26

Y1 - 2022/8/26

N2 - Macrocyclic catalysts having a phenol-acetylene-phenol triad were developed as a hydrogen-bond donor catalyst. The rigid macrocyclic framework suppressed intramolecular hydrogen bonds between neighboring phenolic hydroxy groups. The preorganized phenol-acetylene-phenol moiety formed efficient intermolecular hydrogen bonds with carbonyl groups of substrates. The hydrogen-bond donor catalysts accelerated the Diels-Alder reaction of methyl vinyl ketone with cyclopentadiene. The catalytic ability was higher than that of an acyclic counterpart.

AB - Macrocyclic catalysts having a phenol-acetylene-phenol triad were developed as a hydrogen-bond donor catalyst. The rigid macrocyclic framework suppressed intramolecular hydrogen bonds between neighboring phenolic hydroxy groups. The preorganized phenol-acetylene-phenol moiety formed efficient intermolecular hydrogen bonds with carbonyl groups of substrates. The hydrogen-bond donor catalysts accelerated the Diels-Alder reaction of methyl vinyl ketone with cyclopentadiene. The catalytic ability was higher than that of an acyclic counterpart.

KW - Diels-Alder reactions

KW - Host-guest systems

KW - Hydrogen-bond donor catalysts

KW - Macrocycles

KW - Phenols

UR - http://www.scopus.com/inward/record.url?scp=85128548463&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202200136

DO - 10.1002/ejoc.202200136

M3 - 学術論文

AN - SCOPUS:85128548463

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 32

M1 - e202200136

ER -

Synthesis of Rigid Macrocyclic Phenols and Their Catalytic Applications in Diels-Alder Reactions

Abstract

Keywords

ASJC Scopus subject areas

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