Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones

The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Na...

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Detalles Bibliográficos
Autores principales: Solas, Marta, Suárez‐Pantiga, Samuel, Sanz, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9544548/
https://www.ncbi.nlm.nih.gov/pubmed/35785510
http://dx.doi.org/10.1002/anie.202207406
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author Solas, Marta
Suárez‐Pantiga, Samuel
Sanz, Roberto
author_facet Solas, Marta
Suárez‐Pantiga, Samuel
Sanz, Roberto
author_sort Solas, Marta
collection PubMed
description The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedented enantioselective manner. Excellent enantiomeric ratios and chemical yields are obtained under mild reaction conditions.
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spelling pubmed-95445482022-10-14 Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones Solas, Marta Suárez‐Pantiga, Samuel Sanz, Roberto Angew Chem Int Ed Engl Communications The asymmetric synthesis of cyclopentachromenones from gold‐catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti‐Michael hydroarylation of the ynone moiety to form a gold‐functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedented enantioselective manner. Excellent enantiomeric ratios and chemical yields are obtained under mild reaction conditions. John Wiley and Sons Inc. 2022-07-18 2022-08-26 /pmc/articles/PMC9544548/ /pubmed/35785510 http://dx.doi.org/10.1002/anie.202207406 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Solas, Marta
Suárez‐Pantiga, Samuel
Sanz, Roberto
Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones
title Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones
title_full Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones
title_fullStr Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones
title_full_unstemmed Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones
title_short Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones
title_sort asymmetric gold(i)‐catalyzed tandem hydroarylation–nazarov cyclization: enantioselective access to cyclopentenones
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9544548/
https://www.ncbi.nlm.nih.gov/pubmed/35785510
http://dx.doi.org/10.1002/anie.202207406
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AT suarezpantigasamuel asymmetricgoldicatalyzedtandemhydroarylationnazarovcyclizationenantioselectiveaccesstocyclopentenones
AT sanzroberto asymmetricgoldicatalyzedtandemhydroarylationnazarovcyclizationenantioselectiveaccesstocyclopentenones

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