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Triptycene‐Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group
Author(s) -
Zhang GengWu,
Li PengFei,
Meng Zheng,
Wang HanXiao,
Han Ying,
Chen ChuanFeng
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600911
Subject(s) - enantiopure drug , enantioselective synthesis , group (periodic table) , stereochemistry , methylene , chemistry , molecule , combinatorial chemistry , organic chemistry , catalysis
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.