Citation: Liu Xunshen, Li Meimei, You Jun, Liu Bo. Asymmetric 1, 3-Dipolar Cycloaddition Reaction of C, N-Diarylnitrone with N-α, β-Unsaturated Acylpyrazoles Catalyzed by Ni-DBFOX/Ph[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 86-91. doi: 10.6023/cjoc201608019 shu

Asymmetric 1, 3-Dipolar Cycloaddition Reaction of C, N-Diarylnitrone with N-α, β-Unsaturated Acylpyrazoles Catalyzed by Ni-DBFOX/Ph

Liu Xunshen ,
Li Meimei ,
You Jun ^*,, ,
Liu Bo ^*,,

Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040

Corresponding author: You Jun, Liu Bo,
Received Date: 23 August 2016
Revised Date: 13 September 2016

Fund Project: the National Natural Science Foundation of China 21506043the Innovative Research Team Foundation of Green Chemical Technology in the University of Heilongjiang Province 2014TD007

Figures(1)

Using (R, R)-4, 6-dibenzofurandiyl-2, 2'-bis (4-phenyloxazoline)-Ni (Ni-DBFOX) as the catalyst, asymmetric catalytic 3-dipolar cycloaddition reactions between N-α, β-unsaturated acylpyrazoles and C, N-diarylnitrone have been developed with 95% regioselectivity and an endo/exo ratio of 99:1 with >90% ee of the endo-diastereomer.Influence of olefins, nitrone structure, metal type and amount of catalyst on the reaction stereoselectivity was also carefully discussed.
- asymmetric catalysis,
- 1, 3-dipolar cycloaddition,
- DBFOX/Ph,
- C, N-diarylnitrone,
- N-α, β-unsaturated acylpyrazoles,
- enantioselectivity
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