Nickel-catalyzed asymmetric Ullmann coupling for the synthesis of axially chiral tetra-ortho-substituted biaryl dials

Organic Letters
Wen-Wen ChenGuo-Qiang Lin

Abstract

The first example of nickel-catalyzed asymmetric Ullmann coupling of bis-ortho-substituted arylhalides is described. With the chiral BINOL-based monodentate phosphoramidite ligand, the reaction allows atropoenantioselective synthesis of a series of axially chiral tetra-ortho-substituted biaryl dials. By taking advantage on this asymmetric Ullman coupling as a key stereogenic axis-forming reaction, the formal synthesis of (+)-isoschizandrin was accomplished.

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Citations

May 20, 2017·Chemical Reviews·Joshua E ZweigTimothy R Newhouse
Nov 18, 2017·Chemical Science·Kun Ho Kenny ParkDavid Y-K Chen
Aug 8, 2013·Chemical Society Reviews·Damien CampoloMalek Nechab
Jan 27, 2011·Organic & Biomolecular Chemistry·Caroline A CheethamTimothy W Wallace
Aug 12, 2014·Organic Letters·Huilin LiXuegong She
May 12, 2020·Journal of the American Chemical Society·Hui QiuTian-Sheng Mei

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