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Issue 39, 2017
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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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Article information


Submitted
22 Mar 2017
Accepted
11 Apr 2017
First published
12 Apr 2017

Chem. Commun., 2017,53, 5364-5367
Article type
Communication

Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines

Z. Ling, S. Singh, F. Xie, L. Wu and W. Zhang, Chem. Commun., 2017, 53, 5364
DOI: 10.1039/C7CC02159C

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