Synthesis of Macrocyclic Hexamine from Naphthalene-based C2-Symmetric Chiral Diamine and Dialdehyde

Abstract

Naphthalene-based C2-symmetric chiral diamine was obtained with high enantioselectivity by the double asymmetric addition of diethylzinc to 1,5-dibutoxynaphthalene-2,6-dicarbaldehyde followed by the Mitsunobu azidation and the reduction of azide groups. The dynamic imine formation between the enantiopure C2-symmetric chiral diamine and 1,5-dimethoxynaphthalene-2,6-dicarbaldehyde afforded chiral macrocyclic hexaimine composed of six naphthalene units, which can be reduced to the corresponding hexamine in high yield.