Synthesis of macrocycles containing endocyclic chiral BINAM moieties

A series of nitrogenand oxygen-containing macrocycles with endocyclic chiral BINAM moieties were synthesized using Pd(0)-catalyzed amination with a number of oxadiamines. Two alternative ways to such compounds were compared – from 1,1’-binaphthalene-2,2’-diamine (BINAM) and N,N’-bis(3-bromophenyl) substituted oxadiamine and from N,N’-bis(bromophenyl) substituted 1,1’-binaphthalene-2,2’-diamine and free oxadiamine. Macrocycles containing benzyl and 2,7-disubstituted naphthalene fragments were also successfully synthesized via the second approach, the dependence of their yields on the nature of starting compounds was demonstrated.