Synthesis 2018; 50(09): 1815-1819
DOI: 10.1055/s-0036-1591763
psp
© Georg Thieme Verlag Stuttgart · New York

Dihydroxylation of Olefins with Potassium Permanganate Catalyzed­ by Imidazolium Salt

Imran Khan
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
,
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
,
Anil Valeru
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
,
Yin Xu
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
,
Bin Liu
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
,
Bhavanarushi Sangepu
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
,
Ji-Min Xie*
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, P. R. of China   eMail: luozb@ujs.edu.cn   eMail: xiejm@ujs.edu.cn
› Institutsangaben
The authors acknowledge the financial support of National Natural Science Foundation (No. 21676129), Jiangsu University scientific research funding (13JD062), and Jiangsu Postdoctoral Foundation (1601034B).
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Publikationsverlauf

Received: 19. Dezember 2017

Accepted after revision: 26. Januar 2018

Publikationsdatum:
12. Februar 2018 (online)


Abstract

The development of an efficient and cost-effective cis-di­hydroxylation reaction of acrylate derivatives was achieved. The reaction proceeded in acetone with an imidazolium salt as catalyst to furnish the dihydroxylation of olefins at 0–5 °C using KMnO4 as the oxidant. This efficient and non-aqueous protocol was highly suitable for the large-scale preparation of cis-dihydroxylated compounds from the corresponding acrylate derivatives in high yields without overoxidation.

Supporting Information