Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters

An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficien...

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Detalles Bibliográficos
Autores principales: Chauhan, Pankaj, Mahajan, Suruchi, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4612129/
https://www.ncbi.nlm.nih.gov/pubmed/25563802
http://dx.doi.org/10.1039/c4cc09730k
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author Chauhan, Pankaj
Mahajan, Suruchi
Raabe, Gerhard
Enders, Dieter
author_facet Chauhan, Pankaj
Mahajan, Suruchi
Raabe, Gerhard
Enders, Dieter
author_sort Chauhan, Pankaj
collection PubMed
description An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities.
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spelling pubmed-46121292015-11-09 Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters Chauhan, Pankaj Mahajan, Suruchi Raabe, Gerhard Enders, Dieter Chem Commun (Camb) Chemistry An unprecedented stereoselective organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence between β-dicarbonyl compounds, β-nitroalkenes and 4-nitro-5-styrylisoxazoles sequentially catalyzed by low loading of a squaramide catalyst and an achiral base has been developed. The protocol opens an efficient entry to isoxazole bearing cyclohexanes with six consecutive stereogenic centers including one tetrasubstituted carbon in good yields and excellent diastereo- and enantioselectivities. Royal Society of Chemistry 2015-02-11 2015-01-07 /pmc/articles/PMC4612129/ /pubmed/25563802 http://dx.doi.org/10.1039/c4cc09730k Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Chauhan, Pankaj
Mahajan, Suruchi
Raabe, Gerhard
Enders, Dieter
Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
title Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
title_full Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
title_fullStr Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
title_full_unstemmed Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
title_short Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
title_sort organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4612129/
https://www.ncbi.nlm.nih.gov/pubmed/25563802
http://dx.doi.org/10.1039/c4cc09730k
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