The [3,3]-sigmatropic allyl cyanate/isocyanate rearrangement of glycals in the presence of O-, N-, and C-nucleophiles afforded β-Nglucosyl 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 metalfree methodology represents an excellent and general method for the stereoselective synthesis of N-glycosides and diamino sugars with complete transmission of stereochemical information.

Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1‑Amino and Diamino Sugar Derivatives / Stefania Mirabella, Giulia Petrucci, Cristina Faggi, Camilla Matassini, Francesca Cardona, Andrea Goti. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 22:(2020), pp. 9041-9046. [10.1021/acs.orglett.0c03438]

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

Stefania Mirabella
Membro del Collaboration Group
;
Cristina Faggi
Membro del Collaboration Group
;
Camilla Matassini
Membro del Collaboration Group
;
Francesca Cardona
Membro del Collaboration Group
;
Andrea Goti
2020

Abstract

The [3,3]-sigmatropic allyl cyanate/isocyanate rearrangement of glycals in the presence of O-, N-, and C-nucleophiles afforded β-Nglucosyl 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 metalfree 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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Goal 9: Industry, Innovation, and Infrastructure
Stefania Mirabella, Giulia Petrucci, Cristina Faggi, Camilla Matassini, Francesca Cardona, Andrea Goti
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/1215326
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