Copper(i)-catalyzed asymmetric exo-selective [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones
Chemical Communications2017Vol. 53(58), pp. 8152–8155
Citations Over TimeTop 15% of 2017 papers
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.
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