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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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. |
format | Online Article Text |
id | pubmed-8179366 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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