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Issue 9, 2017
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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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Article information


Submitted
14 Apr 2017
Accepted
25 May 2017
First published
25 May 2017

Org. Chem. Front., 2017,4, 1772-1776
Article type
Research Article

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, 4, 1772
DOI: 10.1039/C7QO00291B

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