Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones

A novel cinchona‐alkaloid‐derived organocatalyst has been developed to catalyze the asymmetric regioselective [3+2] cycloaddition of 3‐isothiocyanato oxindoles with dibenzylidene ketones. A series of spirooxindole enols could be obtained in high yields with good‐to‐excellent diastereo‐ and enantiose...

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Detalles Bibliográficos
Autores principales: Du, Dan, Jiang, Yu, Xu, Qin, Li, Xiao‐Ge, Shi, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4981050/
https://www.ncbi.nlm.nih.gov/pubmed/27547639
http://dx.doi.org/10.1002/open.201600034
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author Du, Dan
Jiang, Yu
Xu, Qin
Li, Xiao‐Ge
Shi, Min
author_facet Du, Dan
Jiang, Yu
Xu, Qin
Li, Xiao‐Ge
Shi, Min
author_sort Du, Dan
collection PubMed
description A novel cinchona‐alkaloid‐derived organocatalyst has been developed to catalyze the asymmetric regioselective [3+2] cycloaddition of 3‐isothiocyanato oxindoles with dibenzylidene ketones. A series of spirooxindole enols could be obtained in high yields with good‐to‐excellent diastereo‐ and enantioselectivities.
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spelling pubmed-49810502016-08-19 Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones Du, Dan Jiang, Yu Xu, Qin Li, Xiao‐Ge Shi, Min ChemistryOpen Communications A novel cinchona‐alkaloid‐derived organocatalyst has been developed to catalyze the asymmetric regioselective [3+2] cycloaddition of 3‐isothiocyanato oxindoles with dibenzylidene ketones. A series of spirooxindole enols could be obtained in high yields with good‐to‐excellent diastereo‐ and enantioselectivities. John Wiley and Sons Inc. 2016-05-25 /pmc/articles/PMC4981050/ /pubmed/27547639 http://dx.doi.org/10.1002/open.201600034 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Du, Dan
Jiang, Yu
Xu, Qin
Li, Xiao‐Ge
Shi, Min
Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
title Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
title_full Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
title_fullStr Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
title_full_unstemmed Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
title_short Enantioselective Synthesis of Spirooxindole Enols: Regioselective and Asymmetric [3+2] Cyclization of 3‐Isothiocyanato Oxindoles with Dibenzylidene Ketones
title_sort enantioselective synthesis of spirooxindole enols: regioselective and asymmetric [3+2] cyclization of 3‐isothiocyanato oxindoles with dibenzylidene ketones
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4981050/
https://www.ncbi.nlm.nih.gov/pubmed/27547639
http://dx.doi.org/10.1002/open.201600034
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