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Issue 12, 2016
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[2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines

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Abstract

A new series of chiral bicyclic 1,2,4-triazolium salts with various substituents in the pseudo-ortho position of the [2.2]paracyclophane skeleton has been successfully synthesized and applied to enantioselective α-silylations of N-tosylaldimines. The dual role of the new carbene precursor as an organocatalyst and as a ligand of the copper catalyst in the asymmetric silylation were investigated. The chiral carbene–copper catalyst has significant advantages over its carbene counterpart as an organocatalyst, affording the corresponding α-silyl amines in 77–99% yields over 20 examples and with 76–98% ee. In addition, the transannular electronic effects of the substituents in the pseudo-ortho position of the [2.2]paracyclophane skeleton were also discussed.

Graphical abstract: [2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines

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Supplementary files

Article information


Submitted
23 Jul 2016
Accepted
26 Sep 2016
First published
27 Sep 2016

Org. Chem. Front., 2016,3, 1725-1737
Article type
Research Article

[2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines

Z. Chen, Y. Huo, P. An, X. Wang, C. Song and Y. Ma, Org. Chem. Front., 2016, 3, 1725
DOI: 10.1039/C6QO00386A

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