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Chem Commun (Camb). 2017 Jul 18;53(58):8152-8155. doi: 10.1039/c7cc03015k.

Copper(i)-catalyzed asymmetric exo-selective [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones.

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Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China.


The employment of β,β-disubstituted enones as dipolarophiles poses a considerable challenge due to their steric hindrance and low reactivity. A copper-catalyzed asymmetric exo-selective dipolar cycloaddition of β-trifluoromethyl β,β-disubstituted enones with azomethine ylides was developed, which provides an efficient access to valuable pyrrolidines bearing a trifluoromethylated all-carbon quaternary stereocenter. Up to quantitative yields with up to >20 : 1 dr and 99% ee were delivered. A broad substrate scope, good functional group tolerance, high stereoselectivity, as well as diverse synthetically valuable transformations of the products make this approach highly attractive.


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