Rhodium-Catalyzed Asymmetric Arylation of N-Sulfonylarylimines by Use of Chiral Diene Ligands. Catalytic Asymmetric Synthesis of Diarylmethylamines.

Abstract

The asymmetric synthesis of diarylmethylamines by the catalytic asymmetric arylation has attracted growing attention due to their importance in biological activity. We have developed new methods of furnishing optically active diarylmethylamines with high yields (>94%) and enantioselectivity (95-99% ee) by use of C2-symmetric chiral diene ligands (Ph-bod* and Ph-bnd*) for the rhodium-catalyzed asymmetric arylation of of N-sulfonylarylimines with arylboroxines in aqueous solvent conditions. These chiral diene ligands showed much higher enantioselectivity and catalytic activity in these arylation reactions than chiral bisphoshine ligands. Under the present reaction conditions, arylboroxines can be used as arylating reagents, which are stable, less toxic, and easily prepared from commercially available arylboronic acids.

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