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Issue 84, 2020
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Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes

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Abstract

The preparation of inherently chiral rigidified calix[4]arenes with an intact cavity is a synthetic challenge due to the complicated synthesis of the starting compounds. Here, we report on a novel strategy for bridging the upper rim of calix[4]arenes consisting in carbonyl group formation and subsequent “extension” into a two-atom bridge using corresponding rearrangement reactions (Baeyer–Villiger, Beckmann). The resulting inherently chiral compounds are potentially applicable in the design of novel receptors. The complexation properties towards selected quaternary ammonium salts were studied by 1H NMR titration. Unusual complexation stoichiometries can be observed depending on the enantiomeric purity (racemic mixture versus pure enantiomers) of an amidic receptor 7 used.

Graphical abstract: Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes

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Supplementary files

Article information


Submitted
06 Aug 2020
Accepted
15 Sep 2020
First published
15 Sep 2020

Chem. Commun., 2020,56, 12773-12776
Article type
Communication

Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes

M. Tlustý, D. Spálovská, M. Kohout, V. Eigner and P. Lhoták, Chem. Commun., 2020, 56, 12773
DOI: 10.1039/D0CC05352J

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