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

Research output: Contribution to journalArticlepeer-review

48 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

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