Literature DB >> 27011062

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

Geng-Wu Zhang1,2, Peng-Fei Li1, Zheng Meng1,2, Han-Xiao Wang1,2, Ying Han1, Chuan-Feng Chen3.   

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.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2016        PMID： 27011062     DOI： 10.1002/anie.201600911

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  20 in total

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2.  Optically active distorted cyclic triptycenes: chiral stationary phases for HPLC.

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Review 7.  Chiral Triptycenes in Supramolecular and Materials Chemistry.

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Journal:  ChemistryOpen       Date:  2020-06-12       Impact factor: 2.911

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9.  A conformationally adaptive macrocycle: conformational complexity and host-guest chemistry of zorb[4]arene.

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10.  Organic core-shell-shaped micro/nanoparticles from twisted macrocycles in Schiff base reaction.

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Journal:  Chem Sci       Date:  2018-10-15       Impact factor: 9.825
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