We describe the synthesis of axially chiral “Buchwald ligand”‐like biphenylphosphines in highly enantioenriched form. These monodentate phosphines, biphenyl analogues of Hayashi's MOP ligands, were evaluated in phosphine‐promoted organocatalysis and in hydrosilylations catalyzed by palladium or by frustrated Lewis pairs. As expected, the title phosphines appeared best suited for transition metal catalysis where they provided higher asymmetric induction.
The trapping of racemic polar carbometallic species with (-)-menthyl ( S)- p-toluenesulfinate (Andersen's reagent) typically proceeds with a very low level of resolution. In this paper, we describe a strategy that allows access to highly atropo-enriched and functionalizable biphenyls by means of Andersen's reagent under kinetic resolution conditions. In particular, useful enantiopure 2-iodobiphenyls could be obtained and were employed in a challenging hypervalent iodine-catalyzed oxidation reaction.
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