SCHEDULED MAINTENANCE
Ene reactions of 2-borylated α-methylstyrenes: a practical route to 4-methylenechromanes and derivatives†
Aurélie
Macé, 
a
Fabienne
Berrée,
a
Thierry
Roisnel,
a
Abdelmadjid
Debache
*b
and
Bertrand
Carboni
*a
a
Fabienne
Berrée,
a
Thierry
Roisnel,
a
Abdelmadjid
Debache
*b
and
Bertrand
Carboni
*a
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.
- This article is part of the themed collection: Synthetic methodology in OBC
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