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Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

A series of benzofulvenes without any electron-withdrawing substituents were employed as 2π-type dipolarophiles for the first time to participate in Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition (1,3-DC) reactions of azomethine ylides. An intrinsic non-benzenoid aromatic characteristic from b...

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Autores principales: Chang, Xin, Liu, Xue-Tao, Li, Fangfang, Yang, Yuhong, Chung, Lung Wa, Wang, Chun-Jiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10207880/
https://www.ncbi.nlm.nih.gov/pubmed/37234882
http://dx.doi.org/10.1039/d3sc00435j
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author Chang, Xin
Liu, Xue-Tao
Li, Fangfang
Yang, Yuhong
Chung, Lung Wa
Wang, Chun-Jiang
author_facet Chang, Xin
Liu, Xue-Tao
Li, Fangfang
Yang, Yuhong
Chung, Lung Wa
Wang, Chun-Jiang
author_sort Chang, Xin
collection PubMed
description A series of benzofulvenes without any electron-withdrawing substituents were employed as 2π-type dipolarophiles for the first time to participate in Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition (1,3-DC) reactions of azomethine ylides. An intrinsic non-benzenoid aromatic characteristic from benzofulvenes serves as a key driving force for activation of the electron-rich benzofulvenes. Utilizing the current methodology, a wide range of multi-substituted chiral spiro-pyrrolidine derivatives containing two contiguous all-carbon quaternary centers were formed in good yield with exclusive chemo-/regioselectivity and high to excellent stereoselectivity. Computational mechanistic studies elucidate the origin of the stereochemical outcome and the chemoselectivity, in which the thermostability of these cycloaddition products is the major factor.
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spelling pubmed-102078802023-05-25 Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides Chang, Xin Liu, Xue-Tao Li, Fangfang Yang, Yuhong Chung, Lung Wa Wang, Chun-Jiang Chem Sci Chemistry A series of benzofulvenes without any electron-withdrawing substituents were employed as 2π-type dipolarophiles for the first time to participate in Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition (1,3-DC) reactions of azomethine ylides. An intrinsic non-benzenoid aromatic characteristic from benzofulvenes serves as a key driving force for activation of the electron-rich benzofulvenes. Utilizing the current methodology, a wide range of multi-substituted chiral spiro-pyrrolidine derivatives containing two contiguous all-carbon quaternary centers were formed in good yield with exclusive chemo-/regioselectivity and high to excellent stereoselectivity. Computational mechanistic studies elucidate the origin of the stereochemical outcome and the chemoselectivity, in which the thermostability of these cycloaddition products is the major factor. The Royal Society of Chemistry 2023-04-25 /pmc/articles/PMC10207880/ /pubmed/37234882 http://dx.doi.org/10.1039/d3sc00435j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chang, Xin
Liu, Xue-Tao
Li, Fangfang
Yang, Yuhong
Chung, Lung Wa
Wang, Chun-Jiang
Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
title Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
title_full Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
title_fullStr Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
title_full_unstemmed Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
title_short Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
title_sort electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10207880/
https://www.ncbi.nlm.nih.gov/pubmed/37234882
http://dx.doi.org/10.1039/d3sc00435j
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