Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides

[Image: see text] A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis...

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Autores principales: Palo-Nieto, Carlos, Sau, Abhijit, Williams, Ryan, Galan, M. Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5309864/
https://www.ncbi.nlm.nih.gov/pubmed/28004941
http://dx.doi.org/10.1021/acs.joc.6b02498
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author Palo-Nieto, Carlos
Sau, Abhijit
Williams, Ryan
Galan, M. Carmen
author_facet Palo-Nieto, Carlos
Sau, Abhijit
Williams, Ryan
Galan, M. Carmen
author_sort Palo-Nieto, Carlos
collection PubMed
description [Image: see text] A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.
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spelling pubmed-53098642017-02-16 Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides Palo-Nieto, Carlos Sau, Abhijit Williams, Ryan Galan, M. Carmen J Org Chem [Image: see text] A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid. American Chemical Society 2016-12-22 2017-01-06 /pmc/articles/PMC5309864/ /pubmed/28004941 http://dx.doi.org/10.1021/acs.joc.6b02498 Text en Copyright © 2016 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
Williams, Ryan
Galan, M. Carmen
Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides
title Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides
title_full Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides
title_fullStr Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides
title_full_unstemmed Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides
title_short Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides
title_sort cooperative brønsted acid-type organocatalysis for the stereoselective synthesis of deoxyglycosides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5309864/
https://www.ncbi.nlm.nih.gov/pubmed/28004941
http://dx.doi.org/10.1021/acs.joc.6b02498
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AT williamsryan cooperativebrønstedacidtypeorganocatalysisforthestereoselectivesynthesisofdeoxyglycosides
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