Cis-2,5-diaminobicyclo[2.2.2]octane, a New Scaffold for Asymmetric Catalysis of the Henry Reaction. Application to the Synthesis of β-Adrenergic Receptor Blocking Agents

A new chiral tetrahydrosalen ligand has been designed and synthesized from cis-2,5-diaminobicyclo[2.2.2]octane.  The complex generated by the interaction of the ligand with (CuOTf)₂.C₆H₅CH₃ is an efficient catalyst for the asymmetric Henry reaction with good stereoselectivity. The Henry reaction catalyzed by this tetrahydrosalen-Cu(I) complex led to syntheses of β-adrenergic blocking agents.