![1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine structure](https://static.chemtradehub.com/structs/121/1218790-44-3-baef.webp "1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine structure")
1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine
CAS Number:
1218790-44-3
Molecular Formula:
C16H26BNO2S
[2.2]Paracyclophane-based N-heterocyclic carbene as efficient catalyst or as ligand for copper catalyst for asymmetric α-silylation of N-tosylaldimines
Literature Information
Publication Date
2016-09-27
DOI
10.1039/C6QO00386A
Impact Factor
5.281
Authors
Yuwen Huo, Ping An, Xichao Wang, Chun Song, Yudao Ma
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
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N-[(R)-[3-(Benzyloxy)-2-(dicyclohexylphosphino)phenyl](phenyl)methyl]-N,2-dimethyl-2-propanesulfinamide
CAS Number:
2565792-50-7
Molecular Formula:
C37H50NO2PS
![2-[2-(2-Methoxyethoxy)ethoxy]-2-methylpropane structure](https://static.chemtradehub.com/structs/527/52788-79-1-71c1.webp "2-[2-(2-Methoxyethoxy)ethoxy]-2-methylpropane structure")
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