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Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition

New types of C(2)-symmetric chiral macrodiolides are readily obtained via chiral N,N′-dioxide-scandium(iii) complex-promoted asymmetric tandem Friedel–Crafts alkylation/intermolecular macrolactonization of ortho-quinone methides with C3-substituted indoles. This protocol provides an array of enantio...

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Autores principales: Xiao, Wanlong, Mo, Yuhao, Guo, Jing, Su, Zhishan, Dong, Shunxi, Feng, Xiaoming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179366/
https://www.ncbi.nlm.nih.gov/pubmed/34164061
http://dx.doi.org/10.1039/d0sc06162j
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author Xiao, Wanlong
Mo, Yuhao
Guo, Jing
Su, Zhishan
Dong, Shunxi
Feng, Xiaoming
author_facet Xiao, Wanlong
Mo, Yuhao
Guo, Jing
Su, Zhishan
Dong, Shunxi
Feng, Xiaoming
author_sort Xiao, Wanlong
collection PubMed
description New types of C(2)-symmetric chiral macrodiolides are readily obtained via chiral N,N′-dioxide-scandium(iii) complex-promoted asymmetric tandem Friedel–Crafts alkylation/intermolecular macrolactonization of ortho-quinone methides with C3-substituted indoles. This protocol provides an array of enantioenriched macrodiolides with 16, 18 or 20-membered rings in moderate to good yields with high diastereoselectivities and excellent enantioselectivities through adjusting the length of the tether at the C3 position of indoles. Density functional theory calculations indicate that the formation of macrocycles is more favorable than that of 9-membered-ring lactones in terms of kinetics and thermodynamics. The potential utility of these intriguing chiral macrodiolide molecules is demonstrated in the enantiomeric recognition of aminols and chemical recognition of metal ions.
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spelling pubmed-81793662021-06-22 Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition Xiao, Wanlong Mo, Yuhao Guo, Jing Su, Zhishan Dong, Shunxi Feng, Xiaoming Chem Sci Chemistry New types of C(2)-symmetric chiral macrodiolides are readily obtained via chiral N,N′-dioxide-scandium(iii) complex-promoted asymmetric tandem Friedel–Crafts alkylation/intermolecular macrolactonization of ortho-quinone methides with C3-substituted indoles. This protocol provides an array of enantioenriched macrodiolides with 16, 18 or 20-membered rings in moderate to good yields with high diastereoselectivities and excellent enantioselectivities through adjusting the length of the tether at the C3 position of indoles. Density functional theory calculations indicate that the formation of macrocycles is more favorable than that of 9-membered-ring lactones in terms of kinetics and thermodynamics. The potential utility of these intriguing chiral macrodiolide molecules is demonstrated in the enantiomeric recognition of aminols and chemical recognition of metal ions. The Royal Society of Chemistry 2020-12-27 /pmc/articles/PMC8179366/ /pubmed/34164061 http://dx.doi.org/10.1039/d0sc06162j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Xiao, Wanlong
Mo, Yuhao
Guo, Jing
Su, Zhishan
Dong, Shunxi
Feng, Xiaoming
Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
title Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
title_full Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
title_fullStr Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
title_full_unstemmed Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
title_short Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
title_sort catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179366/
https://www.ncbi.nlm.nih.gov/pubmed/34164061
http://dx.doi.org/10.1039/d0sc06162j
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