Citation: Jin Lin, Fang Wang, Jing Tian, Jisheng Zhang, Yong Wang, Wei Sun. Theoretical and experimental investigations of the enantioselective epoxidation of olefins catalyzed by manganese complexes[J]. Chinese Chemical Letters, ;2022, 33(3): 1515-1518. doi: 10.1016/j.cclet.2021.08.092 shu

Theoretical and experimental investigations of the enantioselective epoxidation of olefins catalyzed by manganese complexes

Jin Lin ^{a, c} ,
Fang Wang ^a ,
Jing Tian ^{a, c} ,
Jisheng Zhang ^a ,
Yong Wang ^{b, *,} ,
Wei Sun ^{a, c, **,}

a.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China
b.
Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

^**

yong@nbu.edu.cn

wsun@licp.cas.cn

Received Date: 4 June 2021
Revised Date: 17 August 2021
Accepted Date: 19 August 2021
Available Online: 26 August 2021

Figures(6)

The enantioselective epoxidation of olefin by Mn^Ⅱ(R,R-PMCP)(OTf)₂, H₂O₂ and H₂SO₄ was explored by DFT calculations and experiments. Theoretical results suggest that [Mn^Ⅴ(O)(R,R-PMCP)(SO₄)]⁺ species with a triplet ground spin state serves as the active species for the olefin epoxidation. It can be generated by the H₂SO₄ assisted O-O heterolysis of Mn^Ⅲ(OOH) species. Mn^Ⅲ-persulfate is also involved in this system, but it cannot promote the olefin epoxidation directly, preferring instead to transform into Mn^Ⅴ(O). Actually, the asymmetric epoxidation reactions with H₂O₂/H₂SO₄ or Oxone provide similar enantioselectivity in the presence of manganese catalyst. These observations further support the transformation of Mn^Ⅲ-persulfate to Mn^Ⅴ(O) species.
- Epoxidation of olefins,
- Manganese complexes,
- Metal oxo,
- Enantioselective,
- DFT
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