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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 1: 86 - 91

DOI: https://doi.org/10.6023/cjoc201608019

ARTICLE

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
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  • 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

Received date: 2016-08-23

  Revised date: 2016-09-13

  Online published: 2016-09-19

Supported by

Project supported by the National Natural Science Foundation of China(No. 21506043) and the Innovative Research Team Foundation of Green Chemical Technology in the University of Heilongjiang Province(No. 2014TD007).

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Abstract

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.

Key words： asymmetric catalysis; 1,3-dipolar cycloaddition; DBFOX/Ph; C,N-diarylnitrone; N-α,β-unsaturated acylpyrazoles; enantioselectivity

Cite this article

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

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