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Issue 4, 2017
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Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

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Abstract

A Ni(ClO4)2-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal C[double bond, length as m-dash]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%).

Graphical abstract: Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

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Publication details

The article was received on 13 Dec 2016, accepted on 08 Jan 2017, published on 19 Jan 2017 and first published online on 19 Jan 2017


Article type: Edge Article
DOI: 10.1039/C6SC05450A
Citation: Chem. Sci., 2017,8, 2811-2815
  • Open access: Creative Commons BY-NC license
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    Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

    R. Liu, J. Hu, J. Hong, C. Lu, J. Gao and Y. Jia, Chem. Sci., 2017, 8, 2811
    DOI: 10.1039/C6SC05450A

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