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Ene reactions of 2-borylated α-methylstyrenes: a practical route to 4-methylenechromanes and derivatives

Abstract

4-Methylenechromanes were prepared via a three-step process from 2-borylated α-methylstyrenes. This sequence is based on a key glyoxylate-ene reaction catalyzed by scandium(III) triflate. The resulting α-hydroxy boronates, which cyclise to seven-membered homologues of benzoxaborole on silica gel, were cleanly oxidized with sodium perborate, then cyclised under Mitsunobu conditions. Additionally, several further functional transformations of 4-methylenechromanes or their precursors were carried out to illustrate the synthetic potential of these intermediates

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Publication details

The article was received on 26 Apr 2019, accepted on 17 May 2019 and first published on 17 May 2019


Article type: Paper
DOI: 10.1039/C9OB00963A
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Ene reactions of 2-borylated α-methylstyrenes: a practical route to 4-methylenechromanes and derivatives

    C. Boureghda, A. Macé, F. Berrée, T. Roisnel, A. Debache and B. Carboni, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB00963A

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