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Issue 58, 2017
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Copper(I)-catalyzed asymmetric exo-selective [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones

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Abstract

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.

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

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Publication details

The article was received on 19 Apr 2017, accepted on 07 Jun 2017 and first published on 09 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC03015K
Citation: Chem. Commun., 2017,53, 8152-8155
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    Copper(I)-catalyzed asymmetric exo-selective [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones

    B. Xu, Z. Zhang, B. Liu, S. Xu, L. Zhou and J. Zhang, Chem. Commun., 2017, 53, 8152
    DOI: 10.1039/C7CC03015K

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