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Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones
[Image: see text] We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita–Baylis–Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers i...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7161055/ https://www.ncbi.nlm.nih.gov/pubmed/32309713 http://dx.doi.org/10.1021/acsomega.0c00101 |
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author | Lima, Samia R. Coelho, Fernando |
author_facet | Lima, Samia R. Coelho, Fernando |
author_sort | Lima, Samia R. |
collection | PubMed |
description | [Image: see text] We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita–Baylis–Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers in yields higher than 90%. The synthetic usefulness of this protocol was demonstrated by the conversion of selected ketones into biologically valuable α-alkylidene-γ-lactones upon reduction with sodium borohydride. In the course of the scope evaluation, we discovered that this methodology could also furnish α-arylidene-β,γ-butenolides. |
format | Online Article Text |
id | pubmed-7161055 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-71610552020-04-17 Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones Lima, Samia R. Coelho, Fernando ACS Omega [Image: see text] We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita–Baylis–Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers in yields higher than 90%. The synthetic usefulness of this protocol was demonstrated by the conversion of selected ketones into biologically valuable α-alkylidene-γ-lactones upon reduction with sodium borohydride. In the course of the scope evaluation, we discovered that this methodology could also furnish α-arylidene-β,γ-butenolides. American Chemical Society 2020-04-01 /pmc/articles/PMC7161055/ /pubmed/32309713 http://dx.doi.org/10.1021/acsomega.0c00101 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Lima, Samia R. Coelho, Fernando Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones |
title | Synthesis of 1,4,6-Tricarbonyl
Compounds via Regioselective
Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis
of α-Arylidene-butyrolactones |
title_full | Synthesis of 1,4,6-Tricarbonyl
Compounds via Regioselective
Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis
of α-Arylidene-butyrolactones |
title_fullStr | Synthesis of 1,4,6-Tricarbonyl
Compounds via Regioselective
Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis
of α-Arylidene-butyrolactones |
title_full_unstemmed | Synthesis of 1,4,6-Tricarbonyl
Compounds via Regioselective
Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis
of α-Arylidene-butyrolactones |
title_short | Synthesis of 1,4,6-Tricarbonyl
Compounds via Regioselective
Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis
of α-Arylidene-butyrolactones |
title_sort | synthesis of 1,4,6-tricarbonyl
compounds via regioselective
gold(i)-catalyzed alkyne hydration and their application in the synthesis
of α-arylidene-butyrolactones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7161055/ https://www.ncbi.nlm.nih.gov/pubmed/32309713 http://dx.doi.org/10.1021/acsomega.0c00101 |
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