Synthesis of Chiral Macrocycles by Cyclodimerization of Diamines with Stepwise Nucleophilic Aromatic Substitution of 1,5-Difluoro-2,4-dinitrobenzene

Abstract

Chiral cyclophanes were synthesized by cyclodimerization of 2,7-diaza-1,2,3,6,7,8-hexahydropyrene N-acylated with l-amino acids through stepwise nucleophilic aromatic substitution of 1,5-difluoro-2,4-dinitrobenzene.

Key words

macrocycles - chiral - nucleophilic aromatic substitution - cyclophanes - diazapyrene

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Simulations were performed with MMFF force field in chloroform implemented in MacroModel; 20000 conformers were collected for each compound.