Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals

[Image: see text] Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room...

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Autores principales: Palo-Nieto, Carlos, Sau, Abhijit, Galan, M. Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5951607/
https://www.ncbi.nlm.nih.gov/pubmed/28934850
http://dx.doi.org/10.1021/jacs.7b08898
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author Palo-Nieto, Carlos
Sau, Abhijit
Galan, M. Carmen
author_facet Palo-Nieto, Carlos
Sau, Abhijit
Galan, M. Carmen
author_sort Palo-Nieto, Carlos
collection PubMed
description [Image: see text] Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles.
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spelling pubmed-59516072018-05-15 Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals Palo-Nieto, Carlos Sau, Abhijit Galan, M. Carmen J Am Chem Soc [Image: see text] Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles. American Chemical Society 2017-09-21 2017-10-11 /pmc/articles/PMC5951607/ /pubmed/28934850 http://dx.doi.org/10.1021/jacs.7b08898 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Palo-Nieto, Carlos
Sau, Abhijit
Galan, M. Carmen
Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
title Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
title_full Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
title_fullStr Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
title_full_unstemmed Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
title_short Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
title_sort gold(i)-catalyzed direct stereoselective synthesis of deoxyglycosides from glycals
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5951607/
https://www.ncbi.nlm.nih.gov/pubmed/28934850
http://dx.doi.org/10.1021/jacs.7b08898
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