Synthesis of Macrocycles Containing Endocyclic Chiral BINAM Moieties

Olga K. Grigorova, Alexei D. Averin,^@ Olga A. Maloshitskaya, and Irina P. Beletskaya

Lomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia

^@Corresponding author E-mail: alexaveron@yandex.ru

DOI: 10.6060/mhc161071a

Macroheterocycles 2016 9(4) 425-432

A series of nitrogen- and 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.

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