Jump to main content
Jump to site search

Issue 23, 2019
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

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., 2019,17, 5789-5800

  •   Request permissions

    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, 17, 5789
    DOI: 10.1039/C9OB00963A

Search articles by author

Spotlight

Advertisements