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Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry
In this work, we present a strategy for the preparation of functionalized 4H-chromene derivatives via a Cs(2)CO(3)-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl N-phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The produ...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9044656/ https://www.ncbi.nlm.nih.gov/pubmed/35494146 http://dx.doi.org/10.1039/d1ra08323f |
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author | Rouh, Hossein Tang, Yao Zhang, Sai Ali, Ahmed I. M. Surowiec, Kazimierz Unruh, Daniel Li, Guigen |
author_facet | Rouh, Hossein Tang, Yao Zhang, Sai Ali, Ahmed I. M. Surowiec, Kazimierz Unruh, Daniel Li, Guigen |
author_sort | Rouh, Hossein |
collection | PubMed |
description | In this work, we present a strategy for the preparation of functionalized 4H-chromene derivatives via a Cs(2)CO(3)-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl N-phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The products were purified simply by washing the crude mixture with hexanes following the Group-Assisted Purification (GAP) chemistry/technology to bypass traditional separation methods. The absolute configuration was unambiguously determined by X-ray structure analysis. |
format | Online Article Text |
id | pubmed-9044656 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90446562022-04-28 Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry Rouh, Hossein Tang, Yao Zhang, Sai Ali, Ahmed I. M. Surowiec, Kazimierz Unruh, Daniel Li, Guigen RSC Adv Chemistry In this work, we present a strategy for the preparation of functionalized 4H-chromene derivatives via a Cs(2)CO(3)-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl N-phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The products were purified simply by washing the crude mixture with hexanes following the Group-Assisted Purification (GAP) chemistry/technology to bypass traditional separation methods. The absolute configuration was unambiguously determined by X-ray structure analysis. The Royal Society of Chemistry 2021-12-14 /pmc/articles/PMC9044656/ /pubmed/35494146 http://dx.doi.org/10.1039/d1ra08323f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Rouh, Hossein Tang, Yao Zhang, Sai Ali, Ahmed I. M. Surowiec, Kazimierz Unruh, Daniel Li, Guigen Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry |
title | Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry |
title_full | Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry |
title_fullStr | Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry |
title_full_unstemmed | Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry |
title_short | Asymmetric [4 + 2] cycloaddition synthesis of 4H-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry |
title_sort | asymmetric [4 + 2] cycloaddition synthesis of 4h-chromene derivatives facilitated by group-assisted-purification (gap) chemistry |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9044656/ https://www.ncbi.nlm.nih.gov/pubmed/35494146 http://dx.doi.org/10.1039/d1ra08323f |
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