Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter

An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylami...

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Autores principales: Meninno, Sara, Volpe, Chiara, Della Sala, Giorgio, Capobianco, Amedeo, Lattanzi, Alessandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901985/
https://www.ncbi.nlm.nih.gov/pubmed/27340455
http://dx.doi.org/10.3762/bjoc.12.63
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author Meninno, Sara
Volpe, Chiara
Della Sala, Giorgio
Capobianco, Amedeo
Lattanzi, Alessandra
author_facet Meninno, Sara
Volpe, Chiara
Della Sala, Giorgio
Capobianco, Amedeo
Lattanzi, Alessandra
author_sort Meninno, Sara
collection PubMed
description An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylamine was found to be the most effective catalyst when using trans-β-methyl-β-nitrostyrenes affording the heterocyclic products in good yields and moderate stereoselectivities.
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spelling pubmed-49019852016-06-23 Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter Meninno, Sara Volpe, Chiara Della Sala, Giorgio Capobianco, Amedeo Lattanzi, Alessandra Beilstein J Org Chem Letter An investigation on the stereoselective cascade sulfa-Michael/aldol reaction of nitroalkenes and commercially available 1,4-dithiane-2,5-diol to 3,4,5-substituted tetrahydrothiophenes, bearing a quaternary stereocenter, is presented. A secondary amine thiourea derived from (R,R)-1,2-diphenylethylamine was found to be the most effective catalyst when using trans-β-methyl-β-nitrostyrenes affording the heterocyclic products in good yields and moderate stereoselectivities. Beilstein-Institut 2016-04-05 /pmc/articles/PMC4901985/ /pubmed/27340455 http://dx.doi.org/10.3762/bjoc.12.63 Text en Copyright © 2016, Meninno 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
Meninno, Sara
Volpe, Chiara
Della Sala, Giorgio
Capobianco, Amedeo
Lattanzi, Alessandra
Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
title Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
title_full Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
title_fullStr Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
title_full_unstemmed Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
title_short Stereoselective amine-thiourea-catalysed sulfa-Michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
title_sort stereoselective amine-thiourea-catalysed sulfa-michael/nitroaldol cascade approach to 3,4,5-substituted tetrahydrothiophenes bearing a quaternary stereocenter
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4901985/
https://www.ncbi.nlm.nih.gov/pubmed/27340455
http://dx.doi.org/10.3762/bjoc.12.63
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