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

文献情報

出版日 2016-09-27

DOI 10.1039/C6QO00386A

インパクトファクター 5.281

著者

Yuwen Huo, Ping An, Xichao Wang, Chun Song, Yudao Ma

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

[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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