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Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines

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Abstract

A Cu-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines was developed, providing the corresponding chiral α-tertiary amines with up to 98% ee. The method tolerates some variations in cyclic N-sulfonyl ketimine and alkyne scope. These products could be used in several transformations, in particular, the products of 6-membered cyclic N-sulfonyl ketimines could be easily converted to linear chiral α-tertiary amines. This asymmetric alkynylation provides an efficient, gram-scale, low-cost transition-metal catalyzed synthesis of chiral α-tetrasubstituted propargylamines.

Graphical abstract: Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines

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Publication details

The article was received on 22 Mar 2017, accepted on 11 Apr 2017 and first published on 12 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC02159C
Citation: Chem. Commun., 2017, Advance Article
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    Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines

    Z. Ling, S. Singh, F. Xie, L. Wu and W. Zhang, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02159C

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