TY - JOUR
T1 - Photocatalytic Asymmetric Epoxidation of Terminal Olefins Using Water as an Oxygen Source in the Presence of a Mononuclear Non-Heme Chiral Manganese Complex
AU - Shen, Duyi
AU - Saracini, Claudio
AU - Lee, Yong Min
AU - Sun, Wei
AU - Fukuzumi, Shunichi
AU - Nam, Wonwoo
N1 - 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.
PY - 2016/12/14
Y1 - 2016/12/14
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85006256442&partnerID=8YFLogxK
U2 - 10.1021/jacs.6b10836
DO - 10.1021/jacs.6b10836
M3 - Article
C2 - 27960322
AN - SCOPUS:85006256442
VL - 138
SP - 15857
EP - 15860
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 49
ER -