Synthesis of Multisubstituted Cyclohexenes and Cyclopentenes via Cascade Michael/Aldol/Annulative SuFEx/β-Sultone Desulfonation of β-Arylethenesulfonyl Fluorides

Fang Zhang; Qichao Zhang; Pei Xie; Qifan Wang; Lin He; Zhihua Cai; Guangfen Du

doi:10.1039/d5qo00837a

January 1, 2025Organic Chemistry Frontiers

Synthesis of Multisubstituted Cyclohexenes and Cyclopentenes via Cascade Michael/Aldol/Annulative SuFEx/β-Sultone Desulfonation of β-Arylethenesulfonyl Fluorides

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Key Points

The cascade process produces multisubstituted cyclohexenes and cyclopentenes efficiently.
Utilizing γ- and β-ketomalononitriles enhances the reaction yield significantly.
This novel approach integrates multiple synthetic methods including SuFEx transformations.
Implications for organic synthesis underline the potential for more versatile compound creation.

Implication

This method combines Michael addition and aldol reaction in β-arylethenesulfonyl fluorides, suggesting new synthetic pathways.

Abstract

γ- and β-Ketomalononitriles react with β-arylethenesulfonyl fluorides via a cascade Michael addition/aldol reaction/annulative SuFEx/β-sultone desulfonation process to produce multisubstituted cyclohexenes and cyclopentenes.

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Cite This Study

Zhang et al. (2025) studied this question.

synapsesocial.com/papers/68c1afc654b1d3bfb60e7adf https://doi.org/10.1039/d5qo00837a

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Synthesis of Multisubstituted Cyclohexenes and Cyclopentenes via Cascade Michael/Aldol/Annulative SuFEx/β-Sultone Desulfonation of β-Arylethenesulfonyl Fluorides

Key Points

Implication

Abstract

Discussion

Cite This Study

Synthesis of Multisubstituted Cyclohexenes and Cyclopentenes via Cascade Michael/Aldol/Annulative SuFEx/β-Sultone Desulfonation of β-Arylethenesulfonyl Fluorides

Key Points

Implication

Abstract

Discussion

Cite This Study

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