Issue 86, 2020

Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid

Abstract

A novel manganese catalyst bearing an L-proline-derived N4 ligand has been developed for enabling acid-free asymmetric epoxidation of olefins with tert-butyl hydroperoxide as the oxidant. A variety of olefins that are well-matched in size with the ligand pocket can be transformed to epoxides with excellent enantioselectivities. The smaller ligand pocket is also beneficial to the enantioselective epoxidation of simple olefins. Cryospray ionization mass spectrometry experiments reveal that a MnIV[double bond, length as m-dash]O species serves as an active epoxidizing species.

Graphical abstract: Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid

Supplementary files

Article information

Article type
Communication
Submitted
29 Jun 2020
Accepted
11 Sep 2020
First published
17 Sep 2020

Chem. Commun., 2020,56, 13101-13104

Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid

D. Xu, Q. Sun, J. Lin and W. Sun, Chem. Commun., 2020, 56, 13101 DOI: 10.1039/D0CC04440G

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