Citation: 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 shu

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

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, youjunjun@126.com Yu Yanchao, yycyychao@163.com
Received Date: 4 January 2019
Revised Date: 2 March 2019
Available Online: 15 June 2019
Fund Project: Project supported by the Natural Science Foundation of Heilongjiang Province (No. LH2019B010), and the National Natural Science Foundation of China (No. 21506043)the Natural Science Foundation of Heilongjiang Province LH2019B010the National Natural Science Foundation of China 21506043

Figures(2)

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