Triptycene‐Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group,Angewandte Chemie International Edition

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Triptycene‐Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2016-03-24 , DOI: 10.1002/anie.201600911
Geng-Wu Zhang _{1,

2} , Peng-Fei Li ₁ , Zheng Meng _{1,

2} , Han-Xiao Wang _{1,

2} , Ying Han ₁ , Chuan-Feng Chen ₁

Affiliation

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.

中文翻译：

基于三萜烯的手性大环宿主对具有三甲基氨基的手性客体进行高度对映选择性识别

设计并合成了一类由三个亚甲基桥接的手性2,6-二羟基三蝶烯亚基组成的新型手性大环芳烃。结构研究表明，大环分子采用六角螺母样结构，具有螺旋手性腔和高度固定的构象。通过引入手性助剂获得了两个对映纯大环化合物，这些化合物对三对含三甲氨基的手性化合物表现出高对映选择性，从而实现了高效拆分。

更新日期：2016-03-24

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