Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones

The enantioselective construction of densely functionalized cyclopentene bearing contiguous three stereocenters has been a challenging task in organic synthesis. Herein, we present a phoshine-catalyzed highly regio-, diastereo- and enantioselective [3 + 2] cycloaddition of γ-substituted allenoates w...

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Autores principales: Zhou, Wei, Wang, Huamin, Tao, Mengna, Zhu, Chao-Ze, Lin, Tao-Yan, Zhang, Junliang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5590097/
https://www.ncbi.nlm.nih.gov/pubmed/28936335
http://dx.doi.org/10.1039/c7sc01432e
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author Zhou, Wei
Wang, Huamin
Tao, Mengna
Zhu, Chao-Ze
Lin, Tao-Yan
Zhang, Junliang
author_facet Zhou, Wei
Wang, Huamin
Tao, Mengna
Zhu, Chao-Ze
Lin, Tao-Yan
Zhang, Junliang
author_sort Zhou, Wei
collection PubMed
description The enantioselective construction of densely functionalized cyclopentene bearing contiguous three stereocenters has been a challenging task in organic synthesis. Herein, we present a phoshine-catalyzed highly regio-, diastereo- and enantioselective [3 + 2] cycloaddition of γ-substituted allenoates with β-perfluoroalkyl enones, delivering a wide range of densely functionalized perfluoroalkylated cyclopentenes with three contiguous chiral stereocenters.
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spelling pubmed-55900972017-09-21 Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones Zhou, Wei Wang, Huamin Tao, Mengna Zhu, Chao-Ze Lin, Tao-Yan Zhang, Junliang Chem Sci Chemistry The enantioselective construction of densely functionalized cyclopentene bearing contiguous three stereocenters has been a challenging task in organic synthesis. Herein, we present a phoshine-catalyzed highly regio-, diastereo- and enantioselective [3 + 2] cycloaddition of γ-substituted allenoates with β-perfluoroalkyl enones, delivering a wide range of densely functionalized perfluoroalkylated cyclopentenes with three contiguous chiral stereocenters. Royal Society of Chemistry 2017-06-01 2017-04-19 /pmc/articles/PMC5590097/ /pubmed/28936335 http://dx.doi.org/10.1039/c7sc01432e Text en This journal is © The Royal Society of Chemistry 2017 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
Zhou, Wei
Wang, Huamin
Tao, Mengna
Zhu, Chao-Ze
Lin, Tao-Yan
Zhang, Junliang
Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
title Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
title_full Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
title_fullStr Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
title_full_unstemmed Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
title_short Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
title_sort phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5590097/
https://www.ncbi.nlm.nih.gov/pubmed/28936335
http://dx.doi.org/10.1039/c7sc01432e
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AT taomengna phosphinecatalyzedenantioselective32cycloadditionsofgsubstitutedallenoateswithbperfluoroalkylenones
AT zhuchaoze phosphinecatalyzedenantioselective32cycloadditionsofgsubstitutedallenoateswithbperfluoroalkylenones
AT lintaoyan phosphinecatalyzedenantioselective32cycloadditionsofgsubstitutedallenoateswithbperfluoroalkylenones
AT zhangjunliang phosphinecatalyzedenantioselective32cycloadditionsofgsubstitutedallenoateswithbperfluoroalkylenones

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