Chiral ferrocenyl P,S-ligands for highly efficient copper-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides

A series of chiral ferrocenyl P,S-ligands based on benzimidazole and imidazole backbones have been prepared from Ugi's amine through a three-step transformation. These ligands were successfully employed in the Cu-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with various electro...

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Bibliographic Details
Published in:Tetrahedron 2016-05, Vol.72 (21), p.2616-2622
Main Authors: Han, Fu-Zhong, Yu, Sai-Bo, Zhang, Cheng, Hu, Xiang-Ping
Format: Article
Language:English
Subjects:
[3+2]-Cycloaddition
Amines
Asymmetric catalysis
Asymmetry
Azomethine ylide
Chiral P,S-ligand
Copper
Cycloaddition
Imidazole
Ligands
Olefins
Tetrahedrons
Transformations
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Summary:A series of chiral ferrocenyl P,S-ligands based on benzimidazole and imidazole backbones have been prepared from Ugi's amine through a three-step transformation. These ligands were successfully employed in the Cu-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with various electron-deficient olefins, giving the corresponding cycloadducts in high endo-selectivities and excellent enantioselectivities (up to 99% ee). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.01.003