Synthesis of [2.2]paracyclophane-based bidentate oxazoline–carbene ligands for the asymmetric 1,2-silylation of N-tosylaldimines

[Display omitted] A series of novel oxazoline-substituted imidazolium salts with planar and central chirality has been successfully synthesized and applied to copper-catalyzed enantioselective 1,2-silylation of N-tosylaldimines. The oxazoline–carbene copper complex generated in situ by the reaction...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2017-06, Vol.28 (6), p.783-790
Main Authors: Wang, Xichao, Chen, Zhen, Duan, Wenzeng, Song, Chun, Ma, Yudao
Format: Article
Language:English
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Summary:[Display omitted] A series of novel oxazoline-substituted imidazolium salts with planar and central chirality has been successfully synthesized and applied to copper-catalyzed enantioselective 1,2-silylation of N-tosylaldimines. The oxazoline–carbene copper complex generated in situ by the reaction of the oxazoline-substituted imidazolium and Cu2O demonstrated an exceptionally high catalytic activity in the asymmetric 1,2-silylation of N-tosylaldimines, affording chiral α-amino silanes with excellent yields and enantioselectivities.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2017.05.001