Department of Chemistry, Biology, and Environmental Science, Faculty of Science, Nara Women's University, Kitauoyanishi-machi, Nara 630-8506, Japan.
Synthesis Research Laboratory, Kurashiki Research Center, Kuraray Co., Ltd, 2045-1, Sakazu, Kurashiki, Okayama 710-0801, Japan.
Org Biomol Chem. 2022 Jan 19;20(3):570-574. doi: 10.1039/d1ob02277f.
1,1-Disubstituted alkenes feature high steric hindrance, which renders their Wacker-type oxidation difficult. We demonstrate the stereoselective synthesis of 2-hydroxytetrahydrofurans the Wacker-type oxidation of 3-methyl-3-buten-1-ols by using a PdCl(MeCN)/NO/BQ catalyst system under 1 atm O in HO or HO/DMF.
1,1-二取代烯烃具有较大的空间位阻，这使得它们的 Wacker 型氧化反应变得困难。我们通过使用 PdCl(MeCN)/NO/BQ 催化剂体系，在 1 个大气压的 O 气氛下，在 HO 或 HO/DMF 中，实现了 3-甲基-3-丁烯-1-醇的 Wacker 型氧化反应，立体选择性地合成了 2-羟基四氢呋喃。
