%0 Journal Article %T Ene reactions of 2-borylated α-methylstyrenes a practical route to 4-methylenechromanes and derivatives %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Université frères Mentouri Constantine I (UMC) %A Boureghda, Chaima %A Macé, Aurélie %A Berrée, Fabienne %A Roisnel, Thierry %A Debache, Abdelmadjid %A Carboni, Bertrand %Z Université de Rennes 1 %Z Centre National de la Recherche Scientifique %< avec comité de lecture %@ 1477-0520 %J Organic & Biomolecular Chemistry %I Royal Society of Chemistry %V 17 %N 23 %P 5789-5800 %8 2019-06-21 %D 2019 %R 10.1039/c9ob00963a %M 31135020 %Z Chemical SciencesJournal articles %X 4-Methylenechromanes were prepared via a three-step process from 2-borylated -methylstyrenes. This sequence is based on a key glyoxylate-ene reaction catalyzed by scandium(III) triflate. The resulting -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. %G English %2 https://univ-rennes.hal.science/hal-02150447/document %2 https://univ-rennes.hal.science/hal-02150447/file/Ene%20reactions%20of%202-borylated-methylstyrenes_accepted.pdf %L hal-02150447 %U https://univ-rennes.hal.science/hal-02150447 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ ISCR %~ SCR_ICMV %~ SCR-CD %~ STATS-UR1 %~ UR1-SPM %~ ISCR-PRATS %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ ISCR-CORINT %~ UR1-SDLM %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ ISCR-CORINT1 %~ TEST-HALCNRS %~ UR1-MMS %~ TEST2-HALCNRS