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Cu(I)-catalyzed Michael addition of ketiminoesters to β-trifluoromethyl β,β-disubstituted enones: rapid access to 1-pyrrolines bearing a quaternary all-carbon stereocenter

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Abstract

A highly chemo-, diastereo-, and enantioselective Cu(I)/(S,S)-iPr-FOXAP-catalyzed Michael addition of ketiminoester to β-trifluoromethyl β,β-disubstituted enones was developed. This method provides facile access to highly functionalized 1-pyrrolines bearing two contiguous stereocenters, including a trifluoromethylated all-carbon quaternary stereocenter, via one-pot hydrolytic cyclization (up to >20 : 1 cr, > 20 : 1 dr, and 98% ee). The addition of trace amounts of water to the direct 1,3-dipolar cycloaddition is crucial for obtaining 1-pyrrolines with high chemoselectivities rather than pyrrolidines.

Graphical abstract: Cu(i)-catalyzed Michael addition of ketiminoesters to β-trifluoromethyl β,β-disubstituted enones: rapid access to 1-pyrrolines bearing a quaternary all-carbon stereocenter

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Publication details

The article was received on 14 Apr 2017, accepted on 25 May 2017 and first published on 25 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00291B
Citation: Org. Chem. Front., 2017, Advance Article
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    Cu(I)-catalyzed Michael addition of ketiminoesters to β-trifluoromethyl β,β-disubstituted enones: rapid access to 1-pyrrolines bearing a quaternary all-carbon stereocenter

    B. Liu, Z. Zhang, B. Xu, S. Xu, H. Wu, Y. Liu and J. Zhang, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00291B

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