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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 190, 2015 - Issue 8: 26th International Symposium on Organic Chemistry of Sulfur (ISOCS-26)
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Original Articles

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

Quentin DherbassyUniversité de Strasbourg, ECPM, UMR CNRS 7509, SynCat, Strasbourg, France
,
Geoffrey SchwertzUniversité de Strasbourg, ECPM, UMR CNRS 7509, SynCat, Strasbourg, France
,
Chinmoy Kumar HazraUniversité de Strasbourg, ECPM, UMR CNRS 7509, SynCat, Strasbourg, France
,
Thomas WeschUniversité de Strasbourg, ECPM, UMR CNRS 7509, SynCat, Strasbourg, France
,
Joanna Wencel-DelordUniversité de Strasbourg, ECPM, UMR CNRS 7509, SynCat, Strasbourg, FranceCorrespondence[email protected] [email protected]
&
Françoise ColobertUniversité de Strasbourg, ECPM, UMR CNRS 7509, SynCat, Strasbourg, FranceCorrespondence[email protected] [email protected]
Pages 1339-1351 | Received 20 Jan 2015, Accepted 09 Feb 2015, Published online: 03 Aug 2015
 
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GRAPHICAL ABSTRACT

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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