Asymmetric synthesis of dibenzo[<i>b</i>,<i>d</i>]azepines by Cu-catalyzed reductive or borylative cyclization
Patricia Rodríguez‐Salamanca, Rocío Martín-de la Calle, Verónica M Rodríguez, Pedro Merino, Rosario Fernández, José M. Lassaletta, Valentı́n Hornillos
Abstract
/(Ph-BPE)] as the catalyst enables the synthesis of 7-membered bridged biarylamines containing both central and axial stereogenic elements in high yields (up to 98%) and with excellent diastereo- and enantioselectivities (>20 : 1 d.r., up to 99% ee). Moreover, the same catalyst was found to facilitate a related borylative cyclization to afford versatile boronic ester derivatives. Both reactions proceed under mild conditions (rt) and are applicable to a variety of substituted aromatic and heterocyclic derivatives.
Topics & Concepts
CatalysisCopperChemistryCombinatorial chemistryReductive eliminationStereochemistryAxial symmetryMedicinal chemistryPhysicsOrganic chemistryQuantum mechanicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlkaloids: synthesis and pharmacology