Issue 11, 2010
From the journal:

Chemical Society Reviews

Inherently chiral concave molecules—from synthesis to applications

Agnieszka Szumna*a  

* Corresponding authors

a Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw, Poland
E-mail: szumnaa@icho.edu.pl.
Fax: +48 22 632 66 81
Tel: +48 22 343 21 10

Abstract

This tutorial review covers the recent development in the synthesis and application of molecules and finite assemblies that are chiral owing to their curvature. A modified definition of inherent chirality is provided. Various classes of chiral concave molecules are presented including salphen complexes, cyclic amides, derivatives of sumanene, trioxatricornan or subphthalocyanine, cyclotriveratrylenes, homooxacalix[3]arenes, calixarenes, resorcinarenes, phthalocyanines, corannulenes and cavitands. Some of these bowl shaped compounds exhibit high inversion barriers, comparable with the stability of classical carbon chirality centres, while the others (e.g. hydrogen bonded assemblies) can only be detected by NMR. This review is focused on practical aspects of synthesis, resolution and applications in chiral recognition and asymmetric synthesis.

Graphical abstract: Inherently chiral concave molecules—from synthesis to applications

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Article information

DOI
https://doi.org/10.1039/B919527K
Article type
Tutorial Review
Submitted
17 Mar 2010
First published
30 Sep 2010

Chem. Soc. Rev., 2010,39, 4274-4285

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Inherently chiral concave molecules—from synthesis to applications

A. Szumna, Chem. Soc. Rev., 2010, 39, 4274 DOI: 10.1039/B919527K

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