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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 6: 1642 - 1649

DOI: https://doi.org/10.6023/cjoc201901004

Articles

Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex

  • Li Minglong ,
  • Cao Xixian ,
  • You Jun ,
  • Yu Yanchao ,
  • Wu Wenju ,
  • 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: 2019-01-04

  Revised date: 2019-03-02

  Online published: 2019-05-15

Supported by

Project supported by the Natural Science Foundation of Heilongjiang Province (No. LH2019B010), and the National Natural Science Foundation of China (No. 21506043).

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Abstract

Asymmetric cycloaddition reactions catalyzed by Inda-BOX 1 metal complex between two kinds of electron-withdrawing alkenes and C,N-diarylnitrone have been studied respectively. Results showed that the 4-substituted products were mainly obtained in both reactions under the best conditions. When N-acryloyl oxazolidinone was used as dipolarophile, the exo/endo selectivity of the reaction was 100/0, and the ee of the exo product was as high as 97%. When N-acryloyl-3,5-dimethyl pyrazole was used as dipolarophile, the selectivity of exo/endo was 0/100, and the ee of endo product was up to 98%. The relationship of the dipolarophile, the structure of nitrone and the selectivity of the reaction was discussed.

Key words： asymmetric catalysis; 1,3-dipolar cycloaddition reaction; chiral dioxazoline; N-α,β-unsaturated acyl compounds; C,N-diarylnitrone; enantioselectivity

Cite this article

Li Minglong , Cao Xixian , You Jun , Yu Yanchao , Wu Wenju , Liu Bo . Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1642 -1649 . DOI: 10.6023/cjoc201901004

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