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Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization
We report here a sequential enantioselective reduction/C–H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C–H silylation. F...
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/PMC8356817/ https://www.ncbi.nlm.nih.gov/pubmed/34447553 http://dx.doi.org/10.1039/d1sc02119b |
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author | Chen, Jun Shi, Zhan Li, Chunyu Lu, Ping |
author_facet | Chen, Jun Shi, Zhan Li, Chunyu Lu, Ping |
author_sort | Chen, Jun |
collection | PubMed |
description | We report here a sequential enantioselective reduction/C–H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C–H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol. |
format | Online Article Text |
id | pubmed-8356817 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-83568172021-08-25 Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization Chen, Jun Shi, Zhan Li, Chunyu Lu, Ping Chem Sci Chemistry We report here a sequential enantioselective reduction/C–H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C–H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol. The Royal Society of Chemistry 2021-07-05 /pmc/articles/PMC8356817/ /pubmed/34447553 http://dx.doi.org/10.1039/d1sc02119b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Chen, Jun Shi, Zhan Li, Chunyu Lu, Ping Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization |
title | Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization |
title_full | Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization |
title_fullStr | Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization |
title_full_unstemmed | Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization |
title_short | Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/C–H functionalization |
title_sort | catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols via a sequential reduction/c–h functionalization |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8356817/ https://www.ncbi.nlm.nih.gov/pubmed/34447553 http://dx.doi.org/10.1039/d1sc02119b |
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