Issue 3, 2022
From the journal:

Organic & Biomolecular Chemistry

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

Rina Tanaka,a   Saki Komori,a   Yuhei Shimizu,b   Yasutaka Kataokaa  and  Yasuyuki Ura ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Biology, and Environmental Science, Faculty of Science, Nara Women's University, Kitauoyanishi-machi, Nara 630-8506, Japan
E-mail: ura@cc.nara-wu.ac.jp

b Synthesis Research Laboratory, Kurashiki Research Center, Kuraray Co., Ltd, 2045-1, Sakazu, Kurashiki, Okayama 710-0801, Japan

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.

Graphical abstract: Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D1OB02277F
Article type
Communication
Submitted
20 Nov 2021
Accepted
21 Dec 2021
First published
22 Dec 2021

Org. Biomol. Chem., 2022,20, 570-574

Permissions

Request permissions

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

R. Tanaka, S. Komori, Y. Shimizu, Y. Kataoka and Y. Ura, Org. Biomol. Chem., 2022, 20, 570 DOI: 10.1039/D1OB02277F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements