BF3·OEt2-mediated nucleophilic fluorocyclization of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled synthesis of benzofused fluorooxabicyclo[4.2.1]nonanes

Nai-Chen Hsueh; Meng-Yang Chang

doi:10.1039/D2OB01459A

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BF₃·OEt₂-mediated nucleophilic fluorocyclization of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled synthesis of benzofused fluorooxabicyclo[4.2.1]nonanes†

Nai-Chen Hsueh^a and Meng-Yang Chang

*^abc

Author affiliations

* Corresponding authors

^a Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
E-mail: mychang@kmu.edu.tw

^b Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan

^c NPUST College of Professional Studies, National Pingtung University of Science and Technology, Pingtung 912, Taiwan

Abstract

We describe a facile-operational, high-yield method for the diastereocontrolled preparation of novel sulfonyl benzofused fluorooxabicyclo[4.2.1]nonanes by a straightforward synthetic route, including (i) NaBH₄-mediated reduction of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones and (ii) BF₃·OEt₂-mediated intramolecular nucleophilic fluorocyclization. The plausible mechanism for the preparation is proposed and discussed. This protocol can easily install a fluoro-atom on the bridged head position in a short time and under mild conditions, resulting in one carbon–carbon and one carbon–fluorine bond formation.

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Article information

DOI: https://doi.org/10.1039/D2OB01459A
Article type: Paper
Submitted: 10 Aug 2022
Accepted: 08 Sep 2022
First published: 08 Sep 2022

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Org. Biomol. Chem., 2022,20, 7503-7518

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BF₃·OEt₂-mediated nucleophilic fluorocyclization of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled synthesis of benzofused fluorooxabicyclo[4.2.1]nonanes

N. Hsueh and M. Chang, Org. Biomol. Chem., 2022, 20, 7503 DOI: 10.1039/D2OB01459A

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Organic & Biomolecular Chemistry