Steric Tuning of Sulfinamide/Sulfoxides as Chiral Ligands with C1 , Pseudo-meso , and Pseudo-C2 Symmetries: Application in Rhodium(I)-Mediated Arylation

Organic Letters
Lorenzo G BorregoInmaculada Fernández

Abstract

A new family of sulfinamide/sulfoxide derivatives was synthesized as chiral bidentate ligands by stereoselective additions of methylsulfinyl carbanions to N-tert-butylsulfinylimines. The new ligands, with C1, pseudo-meso, and pseudo-C2 symmetries, were successfully assayed in Rh-catalyzed additions of arylboronic acids to activated ketones. The sterically dissymmetric C1 ligand (RS,SC,RS)-N-[1-(phenylsulfinyl)-3-methylbut-2-yl] tert-butylsulfinamide turned out to be the optimal one, allowing the 1,4-additions of diverse arylboronic acids, on different α,β-unsaturated cyclic ketones with high chemical yields and enantioselectivities up to >99% ee.

References

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Apr 27, 2010·Chemical Reviews·Elzbieta Wojaczyńska, Jacek Wojaczyński
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Jan 27, 2012·Organic & Biomolecular Chemistry·Noureddine KhiarInmaculada Fernández
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