Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes.
Rina TanakaSaki KomoriYuhei ShimizuYasutaka KataokaYasuyuki UraPublished in: Organic & biomolecular chemistry (2022)
1,1-Disubstituted alkenes feature high steric hindrance, which renders their Wacker-type oxidation difficult. We demonstrate the stereoselective synthesis of 2-hydroxytetrahydrofurans via the Wacker-type oxidation of 3-methyl-3-buten-1-ols by using a PdCl 2 (MeCN) 2 /NO/BQ catalyst system under 1 atm O 2 in H 2 O or H 2 O/DMF.