Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives

[Image: see text] The [3,3]-sigmatropic allyl cyanate/isocyanate rearrangement of glycals in the presence of O-, N-, and C-nucleophiles afforded β-N-glucosyl and galactosyl carbamates, ureas, and amides in good yields. The unsaturated products were elaborated to N-glycosides by dihydroxylation, to 1...

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Autores principales: Mirabella, Stefania, Petrucci, Giulia, Faggi, Cristina, Matassini, Camilla, Cardona, Francesca, Goti, Andrea
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7735751/
https://www.ncbi.nlm.nih.gov/pubmed/33147974
http://dx.doi.org/10.1021/acs.orglett.0c03438
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author Mirabella, Stefania
Petrucci, Giulia
Faggi, Cristina
Matassini, Camilla
Cardona, Francesca
Goti, Andrea
author_facet Mirabella, Stefania
Petrucci, Giulia
Faggi, Cristina
Matassini, Camilla
Cardona, Francesca
Goti, Andrea
author_sort Mirabella, Stefania
collection PubMed
description [Image: see text] The [3,3]-sigmatropic allyl cyanate/isocyanate rearrangement of glycals in the presence of O-, N-, and C-nucleophiles afforded β-N-glucosyl and galactosyl carbamates, ureas, and amides in good yields. The unsaturated products were elaborated to N-glycosides by dihydroxylation, to 1,3-diaminosugars by tethered aminohydroxylation, or to 1,2-diaminosugars by iteration of the sigmatropic rearrangement. This metal-free methodology represents an excellent and general method for the stereoselective synthesis of N-glycosides and diamino sugars with complete transmission of stereochemical information.
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spelling pubmed-77357512020-12-15 Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives Mirabella, Stefania Petrucci, Giulia Faggi, Cristina Matassini, Camilla Cardona, Francesca Goti, Andrea Org Lett [Image: see text] The [3,3]-sigmatropic allyl cyanate/isocyanate rearrangement of glycals in the presence of O-, N-, and C-nucleophiles afforded β-N-glucosyl and galactosyl carbamates, ureas, and amides in good yields. The unsaturated products were elaborated to N-glycosides by dihydroxylation, to 1,3-diaminosugars by tethered aminohydroxylation, or to 1,2-diaminosugars by iteration of the sigmatropic rearrangement. This metal-free methodology represents an excellent and general method for the stereoselective synthesis of N-glycosides and diamino sugars with complete transmission of stereochemical information. American Chemical Society 2020-11-04 2020-11-20 /pmc/articles/PMC7735751/ /pubmed/33147974 http://dx.doi.org/10.1021/acs.orglett.0c03438 Text en © 2020 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 Mirabella, Stefania
Petrucci, Giulia
Faggi, Cristina
Matassini, Camilla
Cardona, Francesca
Goti, Andrea
Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives
title Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives
title_full Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives
title_fullStr Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives
title_full_unstemmed Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives
title_short Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives
title_sort allyl cyanate/isocyanate rearrangement in glycals: stereoselective synthesis of 1-amino and diamino sugar derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7735751/
https://www.ncbi.nlm.nih.gov/pubmed/33147974
http://dx.doi.org/10.1021/acs.orglett.0c03438
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