Inherently Chiral Upper-Rim-Bridged Calix[4]arenes Possessing a Seven Membered Ring

Martin Tlustý; Petr Slavík; Michal Kohout; Václav Eigner; Pavel Lhoták

doi:10.1021/acs.orglett.7b01170

Inherently Chiral Upper-Rim-Bridged Calix[4]arenes Possessing a Seven Membered Ring

Martin Tlustý, Petr Slavík, Michal Kohout, Václav Eigner, Pavel Lhoták

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The mercuration of calix[4]arene immobilized in the cone conformation allowed the introduction of an amino group at the meta position of the basic skeleton. Acylation and subsequent intramolecular Bischler-Napieralski-type cyclization led to a novel type of bridged calixarene containing a seven-membered ring. These compounds with an enlarged and rigidified cavity represent a unique and inherently chiral system that may potentially be applicable for the design of chiral receptors. The absolute configuration of one enantiomer, obtained by resolution of the racemate using chiral HPLC, was assigned by single-crystal structure determination.

Original language	English
Pages (from-to)	2933-2936
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	11
Early online date	22 May 2017
DOIs	https://doi.org/10.1021/acs.orglett.7b01170
Publication status	Published - 2 Jun 2017

Keywords

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

Access to Document

10.1021/acs.orglett.7b01170

Cite this

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abstract = "The mercuration of calix[4]arene immobilized in the cone conformation allowed the introduction of an amino group at the meta position of the basic skeleton. Acylation and subsequent intramolecular Bischler-Napieralski-type cyclization led to a novel type of bridged calixarene containing a seven-membered ring. These compounds with an enlarged and rigidified cavity represent a unique and inherently chiral system that may potentially be applicable for the design of chiral receptors. The absolute configuration of one enantiomer, obtained by resolution of the racemate using chiral HPLC, was assigned by single-crystal structure determination.",

keywords = "Journal Article, Research Support, Non-U.S. Gov't",

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AU - Tlustý, Martin

AU - Slavík, Petr

AU - Kohout, Michal

AU - Eigner, Václav

AU - Lhoták, Pavel

PY - 2017/6/2

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N2 - The mercuration of calix[4]arene immobilized in the cone conformation allowed the introduction of an amino group at the meta position of the basic skeleton. Acylation and subsequent intramolecular Bischler-Napieralski-type cyclization led to a novel type of bridged calixarene containing a seven-membered ring. These compounds with an enlarged and rigidified cavity represent a unique and inherently chiral system that may potentially be applicable for the design of chiral receptors. The absolute configuration of one enantiomer, obtained by resolution of the racemate using chiral HPLC, was assigned by single-crystal structure determination.

AB - The mercuration of calix[4]arene immobilized in the cone conformation allowed the introduction of an amino group at the meta position of the basic skeleton. Acylation and subsequent intramolecular Bischler-Napieralski-type cyclization led to a novel type of bridged calixarene containing a seven-membered ring. These compounds with an enlarged and rigidified cavity represent a unique and inherently chiral system that may potentially be applicable for the design of chiral receptors. The absolute configuration of one enantiomer, obtained by resolution of the racemate using chiral HPLC, was assigned by single-crystal structure determination.

KW - Journal Article

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

U2 - 10.1021/acs.orglett.7b01170

DO - 10.1021/acs.orglett.7b01170

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JO - Organic Letters

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