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

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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

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Article information


Submitted
29 Jun 2020
Accepted
11 Sep 2020
First published
17 Sep 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

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

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