Enantiopure Sulfoxides: Efficient Chiral Directing Group for Stereoselective C‒H Bond Activation: Towards the Control of Axial Chirality

Quentin Dherbassy,Geoffrey Schwertz,Chinmoy Kumar Hazra,Thomas Wesch,Joanna Wenceldelord,Francoise Colobert

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS（2015）

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Abstract

An application of the S-stereogenic sulfoxide as both, a chiral auxiliary and a directing group, in the context of asymmetric C-H activation, is reported. The atropo-diastereoselective synthesis of a panel of biaryls is achieved via Pd-catalyzed C-C, C-O, and C-I couplings. Moreover, an original mechanistic scenario implying (dynamic) kinetic resolution is evidenced.

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Key words

Sulfoxide,C-H activation,axially chiral biaryl,asymmetric catalysis

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