Triptycene-Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group

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

doi:10.1002/anie.201600911

Triptycene-Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group

Angew Chem Int Ed Engl. 2016 Apr 18;55(17):5304-8. doi: 10.1002/anie.201600911. Epub 2016 Mar 24.

Authors

Geng-Wu Zhang^{1

2}, Peng-Fei Li¹, Zheng Meng^{1

2}, Han-Xiao Wang^{1

2}, Ying Han¹, Chuan-Feng Chen³

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
² University of Chinese Academy of Sciences, Beijing, 100049, China.
³ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China. cchen@iccas.ac.cn.

PMID: 27011062
DOI: 10.1002/anie.201600911

Abstract

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-nut-like 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 trimethylamino group.

Keywords: chiral resolution; enantioselective recognition; host-guest chemistry; macrocycles; triptycenes.

Publication types

Research Support, Non-U.S. Gov't