Issue 19, 2021

An azo-bridged ring system enabled by-standing immobilization of a chiral diene ligand

Abstract

A family of 9-azabicyclo[3.3.1]nonadienes were designed, prepared and successfully applied in the rhodium-catalyzed addition of arylboronic acids to N-tosylarylimines, affording chiral diarylmethyl amides with excellent enantioselectivities (up to 97% ee). The nitrogen atom in the bridged ring enabled a facile immobilization of diene ligands to silica. The obtained heterogeneous catalyst was evaluated in the above addition reaction and reused five times without significant loss in yield and enantioselectivity.

Graphical abstract: An azo-bridged ring system enabled by-standing immobilization of a chiral diene ligand

Supplementary files

Article information

Article type
Research Article
Submitted
06 Jun 2021
Accepted
30 Jul 2021
First published
31 Jul 2021

Org. Chem. Front., 2021,8, 5397-5402

An azo-bridged ring system enabled by-standing immobilization of a chiral diene ligand

Z. Xue, H. Lu, J. Fu, C. Feng and G. Lin, Org. Chem. Front., 2021, 8, 5397 DOI: 10.1039/D1QO00852H

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