Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction

An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with...

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Autores principales: Shu, Tao, Ni, Qijian, Song, Xiaoxiao, Zhao, Kun, Wu, Tianyu, Puttreddy, Rakesh, Rissanen, Kari, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5315016/
https://www.ncbi.nlm.nih.gov/pubmed/26750327
http://dx.doi.org/10.1039/c5cc09581f
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author Shu, Tao
Ni, Qijian
Song, Xiaoxiao
Zhao, Kun
Wu, Tianyu
Puttreddy, Rakesh
Rissanen, Kari
Enders, Dieter
author_facet Shu, Tao
Ni, Qijian
Song, Xiaoxiao
Zhao, Kun
Wu, Tianyu
Puttreddy, Rakesh
Rissanen, Kari
Enders, Dieter
author_sort Shu, Tao
collection PubMed
description An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities.
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spelling pubmed-53150162017-03-01 Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction Shu, Tao Ni, Qijian Song, Xiaoxiao Zhao, Kun Wu, Tianyu Puttreddy, Rakesh Rissanen, Kari Enders, Dieter Chem Commun (Camb) Chemistry An NHC-catalyzed Michael/Michael/esterification domino reaction via homoenolate/enolate intermediates for the asymmetric synthesis of tetrasubstituted cyclopentanes bearing four contiguous stereocenters is described. A variety of α,β-unsaturated aldehydes and 2-nitroallylic acetates react well with good domino yields and high stereoselectivities. Royal Society of Chemistry 2016-02-11 2016-01-05 /pmc/articles/PMC5315016/ /pubmed/26750327 http://dx.doi.org/10.1039/c5cc09581f Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Shu, Tao
Ni, Qijian
Song, Xiaoxiao
Zhao, Kun
Wu, Tianyu
Puttreddy, Rakesh
Rissanen, Kari
Enders, Dieter
Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction
title Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction
title_full Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction
title_fullStr Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction
title_full_unstemmed Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction
title_short Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction
title_sort asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an nhc-catalyzed michael/michael/esterification domino reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5315016/
https://www.ncbi.nlm.nih.gov/pubmed/26750327
http://dx.doi.org/10.1039/c5cc09581f
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