Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes

[Image: see text] α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents a...

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Autores principales: Bernal-Albert, Paloma, Faustino, Hélio, Gimeno, Ana, Asensio, Gregorio, Mascareñas, José L., López, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304836/
https://www.ncbi.nlm.nih.gov/pubmed/25406491
http://dx.doi.org/10.1021/ol503121q
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author Bernal-Albert, Paloma
Faustino, Hélio
Gimeno, Ana
Asensio, Gregorio
Mascareñas, José L.
López, Fernando
author_facet Bernal-Albert, Paloma
Faustino, Hélio
Gimeno, Ana
Asensio, Gregorio
Mascareñas, José L.
López, Fernando
author_sort Bernal-Albert, Paloma
collection PubMed
description [Image: see text] α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.
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spelling pubmed-43048362015-01-27 Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes Bernal-Albert, Paloma Faustino, Hélio Gimeno, Ana Asensio, Gregorio Mascareñas, José L. López, Fernando Org Lett [Image: see text] α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields. American Chemical Society 2014-11-19 2014-12-05 /pmc/articles/PMC4304836/ /pubmed/25406491 http://dx.doi.org/10.1021/ol503121q Text en Copyright © 2014 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 Bernal-Albert, Paloma
Faustino, Hélio
Gimeno, Ana
Asensio, Gregorio
Mascareñas, José L.
López, Fernando
Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
title Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
title_full Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
title_fullStr Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
title_full_unstemmed Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
title_short Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
title_sort gold(i)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: efficient access to highly substituted cyclobutanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304836/
https://www.ncbi.nlm.nih.gov/pubmed/25406491
http://dx.doi.org/10.1021/ol503121q
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