Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high...

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Detalles Bibliográficos
Autores principales: Du, Yonglei, Li, Jian, Chen, Kerong, Wu, Chenglin, Zhou, Yu, Liu, Hong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5530720/
https://www.ncbi.nlm.nih.gov/pubmed/28781700
http://dx.doi.org/10.3762/bjoc.13.131
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author Du, Yonglei
Li, Jian
Chen, Kerong
Wu, Chenglin
Zhou, Yu
Liu, Hong
author_facet Du, Yonglei
Li, Jian
Chen, Kerong
Wu, Chenglin
Zhou, Yu
Liu, Hong
author_sort Du, Yonglei
collection PubMed
description The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high atom economy, and high catalytic asymmetry, thus representing a versatile approach to the synthesis of highly enantioenriched spirocyclopentaneoxindoles.
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spelling pubmed-55307202017-08-04 Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions Du, Yonglei Li, Jian Chen, Kerong Wu, Chenglin Zhou, Yu Liu, Hong Beilstein J Org Chem Full Research Paper The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high atom economy, and high catalytic asymmetry, thus representing a versatile approach to the synthesis of highly enantioenriched spirocyclopentaneoxindoles. Beilstein-Institut 2017-07-07 /pmc/articles/PMC5530720/ /pubmed/28781700 http://dx.doi.org/10.3762/bjoc.13.131 Text en Copyright © 2017, Du et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Full Research Paper
Du, Yonglei
Li, Jian
Chen, Kerong
Wu, Chenglin
Zhou, Yu
Liu, Hong
Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
title Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
title_full Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
title_fullStr Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
title_full_unstemmed Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
title_short Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
title_sort construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric michael–henry cascade reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5530720/
https://www.ncbi.nlm.nih.gov/pubmed/28781700
http://dx.doi.org/10.3762/bjoc.13.131
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