The Diels-Alder reaction of 1,4-quinones in hexafluoroisopropanol

The Diels-Alder reaction of quinones is both of historical and current importance, and numerous asymmetric and catalytic versions have been described. Herein we describe the dramatic rate enhancement observed in the Diels-Alder reactions of a large variety of quinones with moderately activated diene...

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Bibliographic Details
Published inARKIVOC free online journal of organic chemistry Vol. 2024; no. 5
Main Authors Jeanmart, Loïc, Mambourg, Kalina, Hanquet, Gilles, Lanners, Steve
Format Journal Article
LanguageEnglish
Published Arkat USA Inc 01.01.2024
Subjects
Chemical Sciences
hexafluoroisopropanol
quinones
asymmetric synthesis
Diels-Alder reaction
sulfinylquinones
Diels-Alder reaction quinones hexafluoroisopropanol sulfinylquinones asymmetric synthesis
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Summary:The Diels-Alder reaction of quinones is both of historical and current importance, and numerous asymmetric and catalytic versions have been described. Herein we describe the dramatic rate enhancement observed in the Diels-Alder reactions of a large variety of quinones with moderately activated dienes when hexafluoroisopropanol is used as a solvent, even allowing reactions that are not observed in dichloromethane. When chiral sulfinylquinones are used, hexafluoroisopropanol has a marked effect on stereoselectivity. Since the Diels-Alder reactions of sulfinylquinones are known to be an entry into several classes of natural products, and many other quinone cycloadditions have found widespread use in synthesis, the findings described herein will further facilitate their application.
ISSN:1551-7012
1551-7004
1551-7012
DOI:10.24820/ark.5550190.p012.140