Application of Rh(I)/Bicyclo[2.2.1]heptadiene Catalysts to the Enantioselective Synthesis of Chiral Amines

The development of efficient synthetic methods for accessing enantioenriched alpha-chiral amines is of great importance in the disciplines of medicinal and synthetic organic chemistry. Enantioselective Rh-catalyzed 1,2-addition reactions to activated imine derivatives are regarded as useful protocols for forming alpha-chiral amines. This personal account outlines our efforts to develop chiral bicyclo[2.2.1]heptadiene ligands for Rh-catalyzed asymmetric additions of various organoboron reagents to a wide range of imine derivatives. Transformations of the thus-obtained adducts into known natural products or molecules of pharmaceutical importance serve to confirm their synthetic usefulness.

Automated summary

This paper introduces the development of new chiral bicyclo[2.2.1]heptadiene ligands for Rh-catalyzed asymmetric additions of various organoboron reagents to imine derivatives, leading to the formation of enantioenriched alpha-chiral amines. The transformation of the adducts into known natural products or molecules of pharmaceutical importance confirms the synthetic usefulness of this method.