- Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imines: The Expanded Scope and Mechanism Insights
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The mechanism of the Cu(I)/(S,Rp)-PPFOMe-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with fluorinated aldimines has been studied using labeling experiments, control experiments, and linear effect experiments, which clearly ruled out the 1,3-DC/epimerization pathways and explained the unusal exo′-selective stereochemistry. This protocol allows for the preparation of a series of highly functionalized fluorinated imidazolidines in good yields with excellent stereoselectivities. Moreover, the current methods have been successfully extended to synthesize more challenging imidazolidines bearing a CF3-containing quaternary stereogenic center via the endo-selective 1,3-DC of azomethine ylides with trifluorinated ketimine under identical reaction conditions.
- Wei, Liang,Li, Qing-Hua,Wang, Chun-Jiang
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p. 11814 - 11824
(2018/09/21)
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- Asymmetric construction of fluorinated imidazolidines via Cu(i)-catalyzed exo′-selective 1,3-dipolar cycloaddition of azomethine ylides with fluorinated imines
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Expedient access to optically active fluorinated 2,4-trans-imidazolidines was successfully developed via Cu(i)-catalyzed exo′-selective 1,3-DC of azomethine ylides with fluorinated imines.
- Li, Qing-Hua,Wei, Liang,Chen, Xuan,Wang, Chun-Jiang
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supporting information
p. 6277 - 6279
(2013/08/23)
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- Asymmetric construction of fluorinated imidazolidines via Cu(i)-catalyzed exo′-selective 1,3-dipolar cycloaddition of azomethine ylides with fluorinated imines
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Expedient access to optically active fluorinated 2,4-trans-imidazolidines was successfully developed via Cu(i)-catalyzed exo′-selective 1,3-DC of azomethine ylides with fluorinated imines.
- Li, Qing-Hua,Wei, Liang,Chen, Xuan,Wang, Chun-Jiang
-
supporting information
p. 6277 - 6279
(2013/08/23)
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