Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space

The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent....

Descripción completa

Detalles Bibliográficos
Autores principales: Herbert, Simon A, van Laeren, Laura J, Castell, Dominic C, Arnott, Gareth E
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273304/
https://www.ncbi.nlm.nih.gov/pubmed/25550740
http://dx.doi.org/10.3762/bjoc.10.291
_version_ 1782349827330277376
author Herbert, Simon A
van Laeren, Laura J
Castell, Dominic C
Arnott, Gareth E
author_facet Herbert, Simon A
van Laeren, Laura J
Castell, Dominic C
Arnott, Gareth E
author_sort Herbert, Simon A
collection PubMed
description The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji–Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds.
format Online
Article
Text
id pubmed-4273304
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-42733042014-12-30 Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space Herbert, Simon A van Laeren, Laura J Castell, Dominic C Arnott, Gareth E Beilstein J Org Chem Letter The diastereoselective oxazoline-directed lithiation of calix[4]arenes is reported with diastereoselective ratios of greater than 100:1 in some instances. Notably, it has been found that the opposite diastereomer can be accessed via this approach merely through the choice of an alkyllithium reagent. The inherently chiral oxazoline calix[4]arenes have also been preliminarily examined as ligands in the palladium-catalyzed Tsuji–Trost allylation reaction, returning results comparable to their planar chiral ferrocene counterparts pointing towards future application of these types of compounds. Beilstein-Institut 2014-11-25 /pmc/articles/PMC4273304/ /pubmed/25550740 http://dx.doi.org/10.3762/bjoc.10.291 Text en Copyright © 2014, Herbert et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Herbert, Simon A
van Laeren, Laura J
Castell, Dominic C
Arnott, Gareth E
Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
title Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
title_full Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
title_fullStr Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
title_full_unstemmed Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
title_short Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
title_sort inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273304/
https://www.ncbi.nlm.nih.gov/pubmed/25550740
http://dx.doi.org/10.3762/bjoc.10.291
work_keys_str_mv AT herbertsimona inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace
AT vanlaerenlauraj inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace
AT castelldominicc inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace
AT arnottgarethe inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace

Ejemplares similares