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Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

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Abstract

Enantioselective alkynylation of cyclic N-sulfonyl α-ketiminoesters with terminal alkynes was developed by using an Ni(ClO4)2/(R)-DTBM-Segphos complex as a catalyst. A range of propargylic amides bearing quaternary stereocenters were afforded in excellent enantioselectivities (up to 97% ee). Theoretical studies revealed that this reaction proceeded via a Friedel–Crafts-type reaction pathway.

Graphical abstract: Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

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Publication details

The article was received on 08 Feb 2017, accepted on 10 May 2017 and first published on 10 May 2017


Article type: Communication
DOI: 10.1039/C7CC01015J
Citation: Chem. Commun., 2017, Advance Article
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    Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

    R. Liu, L. Zhu, J. Hu, C. Lu, J. Gao, Y. Lan and Y. Jia, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01015J

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