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

Chaima Boureghda; Aurélie Macé; Fabienne Berrée; Thierry Roisnel; Abdelmadjid Debache; Bertrand Carboni

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

Chaima Boureghda ¹ Aurélie Macé ¹ Fabienne Berrée ¹ Thierry Roisnel ¹ Abdelmadjid Debache ² Bertrand Carboni ¹

1 ISCR - Institut des Sciences Chimiques de Rennes

2 UMC - Université Mentouri Constantine [Algérie]

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 γ-hydroxy boronates, which cyclise to seven-membered homologues of benzoxaborole on silica gel, were cleanly oxidized with sodium perborate, and 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.

Document type :

Journal articles

Domain :

Chemical Sciences

Complete list of metadatas

https://hal-univ-rennes1.archives-ouvertes.fr/hal-02150447
Contributor : Laurent Jonchère <>
Submitted on : Friday, June 7, 2019 - 11:42:47 AM
Last modification on : Friday, June 14, 2019 - 1:39:06 PM

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

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

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