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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...

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Autores principales: Lima, Samia R., Coelho, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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.
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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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