Citation: Yi-Nan Li, Xin Chang, Qi Xiong, Xiu-Qin Dong, Chun-Jiang Wang. Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides: Efficient access to chiral pyrrolidine-3-sulfonyl fluorides[J]. Chinese Chemical Letters, ;2021, 32(12): 4029-4032. doi: 10.1016/j.cclet.2021.05.063 shu

Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides: Efficient access to chiral pyrrolidine-3-sulfonyl fluorides

Yi-Nan Li ^a ,
Xin Chang ^a ,
Qi Xiong ^a ,
Xiu-Qin Dong ^{a, c, *,} ,
Chun-Jiang Wang ^{a, b, *,}

a.
Engineering Research Centre of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China
b.
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
c.
Suzhou Institute of Wuhan University, Suzhou 215123, China

xiuqindong@whu.edu.cn

cjwang@whu.edu.cn

Received Date: 30 March 2021
Revised Date: 26 May 2021
Accepted Date: 27 May 2021
Available Online: 2 June 2021

Figures(3)

Cu-catalyzed endo-selective asymmetric 1,3-dipolar cycloaddition of azomethine ylides with ethenesulfonyl fluorides (ESFs) was successfully developed, this protocol provided an efficient and facile method to a wide range of chiral pyrrolidine-3-sulfonyl fluorides with good to excellent results (up to 87% yield, > 20:1 dr, 94% ee). Some other chiral sulfonyl derivatives, such as sulfonamide and sulfonate, were easily accessible through simple transformations with high yields, which demonstrated that the cycloaddition products could be synthetically useful in the sulfur(Ⅵ) fluoride exchange (SuFEx) chemistry.
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