Design, synthesis and applications of new families of chiral sulfonic acids
Authors (5): P. Jakubec, M. E. Muratore, I. Aillaud, A. L. Thompson, D. J. Dixon
Themes: Transformations
DOI: 10.1016/j.tetasy.2015.02.002
Citations: 8
Pub type: journal-article
Pub year: 2015

Publisher: Elsevier BV

Issue: 5-6

License: [{"start"=>{"date-parts"=>[[2015, 3, 1]], "date-time"=>"2015-03-01T00:00:00Z", "timestamp"=>1425168000000}, "content-version"=>"tdm", "delay-in-days"=>0, "URL"=>"https://www.elsevier.com/tdm/userlicense/1.0/"}, {"start"=>{"date-parts"=>[[2015, 12, 10]], "date-time"=>"2015-12-10T00:00:00Z", "timestamp"=>1449705600000}, "content-version"=>"vor", "delay-in-days"=>284, "URL"=>"http://creativecommons.org/licenses/by/4.0/"}]

Publication date(s): 2015/03 (online)

Pages: 251-261

Volume: 26 Issue: 5-6

Journal: Tetrahedron: Asymmetry

Link: [{"URL"=>"https://api.elsevier.com/content/article/PII:S0957416615000579?httpAccept=text/xml", "content-type"=>"text/xml", "content-version"=>"vor", "intended-application"=>"text-mining"}, {"URL"=>"https://api.elsevier.com/content/article/PII:S0957416615000579?httpAccept=text/plain", "content-type"=>"text/plain", "content-version"=>"vor", "intended-application"=>"text-mining"}]

URL: http://dx.doi.org/10.1016/j.tetasy.2015.02.002

Two new families of chiral arenesulfonic acids were synthesised in a short, robust and scalable synthetic sequence involving a key cross-coupling step of an aromatic scaffold with a suitable chiral auxiliary. The flexibility of the synthetic route and the ready availability of a range of naturally occurring chiral auxiliaries allowed us to prepare nine enantiomerically pure sulfonic acids with a tunable stereochemical environment. Application of the strong chiral Brønsted acids was demonstrated in an enantioselective nitrone/enol ether 1,3-dipolar cycloaddition.

Name Description Publised
CCDC 1027606: Experimental Crystal Structure Determination Related Article: Pavol Jakubec, Michael E. Muratore, Isabelle Aillaud, A... 2017


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