Enantioselective Insertion of Metal Carbenes into N[BOND]H Bonds: A Potentially Versatile Route to Chiral Amine Derivatives

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Abstract

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Back to copper: The Rh-catalyzed reactions of diazocarbonyl compounds with amines, leading to N[BOND]H insertion products, have found wide application. However, an enantioselective variant has remained elusive. A return to copper catalysis, first reported for carbene N[BOND]H insertions over 50 years ago, in the presence of chiral ligands and a large noncoordinating counterion, has resulted in enantioselective N[BOND]H insertion into anilines.

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