Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-trifluoromethyl-substituted alkenyl heteroarenes
|Corresponding Author||Chung，Lung Wa; Teng，Huailong|
Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and β-trifluoromethyl-substituted alkenyl heteroarenes was developed for the first time. A wide range of enantioenriched pyrrolidines containing both heteroarenes and trifluoromethyl group with multiple stereogenic centers could be readily accessible by this method with good to high yields and excellent levels of both stereo- and regioselectivity (up to 99% yield, >20:1 rr, >20:1 dr, and up to 95% ee). Notably, substrate-controlled umpolung-type dipolar cycloaddition was also disclosed in this protocol to achieve regiodivergent synthesis with α-aryl substituted aldimine esters as the dipole precursors. Systematic DFT studies were conducted to explore the origin of the stereo- and regioselectivity of this 1,3-dipolar cycloaddition, and suggest that copper(II) salt utilized in this catalytic system could be reduced in-situ to the active copper(I) species and might be responsible for the observed high stereo- and regioselectivity.
National Natural Science Foundation of China["22071186","22071187","22073067","22101216","22271226","21933003","22193020","22193023"] ; Natural Science Foundation of Hubei Province[2020CFA036 2021CFA069] ; Fundamental Research Funds for the Central Universities["2042022kf1180","2042022kf1040"] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Guangdong Provincial Key Laboratory of Catalytic Chemistry[2020B121201002]
|WOS Research Area|
|WOS Accession No|
Cited Times [WOS]:0
|Document Type||Journal Article|
|Department||Department of Chemistry|
1.College of Chemistry and Molecular Sciences,Wuhan University,Wuhan,430072,China
2.State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Shanghai,230021,China
3.Shenzhen Grubbs Institute,Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
4.College of Science,Huazhong Agricultural University,Wuhan,430070,China
|Corresponding Author Affilication||Department of Chemistry; Shenzhen Grubbs Institute|
|First Author's First Affilication||Department of Chemistry; Shenzhen Grubbs Institute|
Cheng，Xiang,Chang，Xin,Yang，Yuhong,et al. Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-trifluoromethyl-substituted alkenyl heteroarenes[J]. Science China Chemistry,2023.
Cheng，Xiang.,Chang，Xin.,Yang，Yuhong.,Zhang，Zongpeng.,Li，Jing.,...&Wang，Chun Jiang.(2023).Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-trifluoromethyl-substituted alkenyl heteroarenes.Science China Chemistry.
Cheng，Xiang,et al."Copper-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-trifluoromethyl-substituted alkenyl heteroarenes".Science China Chemistry (2023).
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