Photocatalytic Asymmetric Epoxidation of Terminal Olefins Using Water as an Oxygen Source in the Presence of a Mononuclear Non-Heme Chiral Manganese Complex

Duyi Shen, Claudio Saracini, Yong Min Lee, Wei Sun, Shunichi Fukuzumi, Wonwoo Nam

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59 Scopus citations

Abstract

Photocatalytic enantioselective epoxidation of terminal olefins using a mononuclear non-heme chiral manganese catalyst, [(R,R-BQCN)MnII]2+, and water as an oxygen source yields epoxides with relatively high enantioselectivities (e.g., up to 60% enantiomeric excess). A synthetic mononuclear non-heme chiral Mn(IV)-oxo complex, [(R,R-BQCN)MnIV(O)]2+, affords similar enantioselectivities in the epoxidation of terminal olefins under stoichiometric reaction conditions. Mechanistic details of each individual step of the photoinduced catalysis, including formation of the Mn(IV)-oxo intermediate, are discussed on the basis of combined results of laser flash photolysis and other spectroscopic methods.

Original languageEnglish
Pages (from-to)15857-15860
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number49
DOIs
StatePublished - 14 Dec 2016

Bibliographical note

Funding Information:
This work was supported by the NRF of Korea through the CRI (NRF-2012R1A3A2048842 to W.N.) and GRL (NRF- 2010-00353 to W.N.) Programs, JSPS KAKENHI (16H02268 to S.F.), and the National Natural Science Foundation of China (21473226 to W.S.). C.S. is grateful for research support from the National Research Foundation of Korea (Grant NRF- 2015H1D3A1066507).

Publisher Copyright:
© 2016 American Chemical Society.

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