Atroposelective synthesis of configurationally stable nonbiaryl N–C atropisomers through direct asymmetric aminations of 1,3-benzenediamines

Abstract

A highly atroposelective synthesis of nonbiaryl N-C atropisomers was achieved via direct aminations of 1,3-benzenediamines with azodicarboxylates enabled by chiral phosphoric acid catalysis. A series of N-substituents, benzene-substituents and azodicarboxylates were well tolerated, generating N-C atropisomers with high configurational stability. The facile derivatizations and utilizations of the chiral products as novel chiral organocatalysts demonstrate the value of these reactions.

Topics & Concepts