Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes†,10.1039/D1OB02277F

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Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes†

Rina Tanaka,Saki Komori,Yuhei Shimizu,Yasutaka Kataoka,Yasuyuki Ura

Organic & Biomolecular Chemistry Pub Date : 12/22/2021 00:00:00 , DOI:10.1039/D1OB02277F

Abstract

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 PdCl₂(MeCN)₂/NO/BQ catalyst system under 1 atm O₂ in H₂O or H₂O/DMF.