Geng-Wu Zhang, Peng-Fei Li, Zheng Meng, Han-Xiao Wang, Ying Han, and Chuan-Feng Chen*

A new class of chiral macrocyclic arene composed of three chiral 2,6-dihydroxyltriptycene subunits bridged by methylene groups was designed and synthesized. Structural studies showed that the macrocyclic molecule adopts a hex-nutlike structure with a helical chiral cavity and highly fixed conformation. Efficient resolution was achieved through the introduction of chiral auxiliaries to give a couple of enantiopure macrocycles, which exhibited high enantioselectivity towards three pairs of chiral compounds containing a trimethylamine group.

This work has been published in Angew. Chem. Int. Ed. 2016, 55, 5304-5308.