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

doi:10.6023/cjoc201608019

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 86-91.DOI: 10.6023/cjoc201608019 Previous Articles Next Articles

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Ni-DBFOX/Ph催化N-α,β-不饱和酰基吡唑与C,N-二芳基硝酮的不对称1,3-偶极环加成反应

刘迅绅, 李美美, 由君, 刘波

哈尔滨理工大学化学与环境工程学院绿色化工技术黑龙江省高校重点实验室哈尔滨 150040

收稿日期:2016-08-23 修回日期:2016-09-13 发布日期:2016-09-19
通讯作者: 由君, 刘波 E-mail:youjunjun@126. com
基金资助:
国家自然科学基金（No. 21506043）和黑龙江省绿色化工技术创新团队（No. 2014TD007）资助项目.

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

Received:2016-08-23 Revised:2016-09-13 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).

1. Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acylpyrazoles Catalyzed by Ni-DBFOX/Ph.PDF(1616KB)

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]. Chin. J. Org. Chem., 2017, 37(1): 86-91.

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Ni-DBFOX/Ph催化N-α,β-不饱和酰基吡唑与C,N-二芳基硝酮的不对称1,3-偶极环加成反应

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

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