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....

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Main Authors:	Simon A. Herbert, Laura J. van Laeren, Dominic C. Castell, Gareth E. Arnott
Format:	Article
Language:	English
Published:	Beilstein-Institut 2014-11-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	calix[4]arene inherently chiral ortholithiation oxazoline Tsuji–Trost
Online Access:	https://doi.org/10.3762/bjoc.10.291

id	doaj-7769d50fa93940128d081b678c84a55e
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spelling	doaj-7769d50fa93940128d081b678c84a55e2021-02-02T01:57:44ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-11-011012751275510.3762/bjoc.10.2911860-5397-10-291Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral spaceSimon A. Herbert0Laura J. van Laeren1Dominic C. Castell2Gareth E. Arnott3Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South AfricaDepartment of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South AfricaDepartment of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South AfricaDepartment of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7602, South AfricaThe 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.https://doi.org/10.3762/bjoc.10.291calix[4]areneinherently chiralortholithiationoxazolineTsuji–Trost
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Simon A. Herbert Laura J. van Laeren Dominic C. Castell Gareth E. Arnott
spellingShingle	Simon A. Herbert Laura J. van Laeren Dominic C. Castell Gareth E. Arnott Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space Beilstein Journal of Organic Chemistry calix[4]arene inherently chiral ortholithiation oxazoline Tsuji–Trost
author_facet	Simon A. Herbert Laura J. van Laeren Dominic C. Castell Gareth E. Arnott
author_sort	Simon A. Herbert
title	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_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_sort	inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2014-11-01
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.
topic	calix[4]arene inherently chiral ortholithiation oxazoline Tsuji–Trost
url	https://doi.org/10.3762/bjoc.10.291
work_keys_str_mv	AT simonaherbert inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace AT laurajvanlaeren inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace AT dominicccastell inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace AT garethearnott inherentlychiralcalix4arenesviaoxazolinedirectedortholithiationsynthesisandprobeofchiralspace
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Inherently chiral calix[4]arenes via oxazoline directed ortholithiation: synthesis and probe of chiral space

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