Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation

[Image: see text] A novel stereoselective synthetic approach to pentahydroxyazepane iminosugars is described. The strategy relies on a key osmium-catalyzed aminohydroxylation reaction of allylic alcohols obtained via addition of vinylmagnesium bromide to a d-mannose-derived aldehyde, which forms the...

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Autores principales: Martínez-Bailén, Macarena, Matassini, Camilla, Clemente, Francesca, Faggi, Cristina, Goti, Andrea, Cardona, Francesca
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10425973/
https://www.ncbi.nlm.nih.gov/pubmed/37515782
http://dx.doi.org/10.1021/acs.orglett.3c02087
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author Martínez-Bailén, Macarena
Matassini, Camilla
Clemente, Francesca
Faggi, Cristina
Goti, Andrea
Cardona, Francesca
author_facet Martínez-Bailén, Macarena
Matassini, Camilla
Clemente, Francesca
Faggi, Cristina
Goti, Andrea
Cardona, Francesca
author_sort Martínez-Bailén, Macarena
collection PubMed
description [Image: see text] A novel stereoselective synthetic approach to pentahydroxyazepane iminosugars is described. The strategy relies on a key osmium-catalyzed aminohydroxylation reaction of allylic alcohols obtained via addition of vinylmagnesium bromide to a d-mannose-derived aldehyde, which forms the new C–N bond with complete regio- and stereocontrol according to the tethering approach. Subsequent intramolecular reductive amination afforded the desired azepanes. This method represents the first application of the osmium-catalyzed tethered aminohydroxylation reaction to the synthesis of iminosugars.
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spelling pubmed-104259732023-08-16 Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation Martínez-Bailén, Macarena Matassini, Camilla Clemente, Francesca Faggi, Cristina Goti, Andrea Cardona, Francesca Org Lett [Image: see text] A novel stereoselective synthetic approach to pentahydroxyazepane iminosugars is described. The strategy relies on a key osmium-catalyzed aminohydroxylation reaction of allylic alcohols obtained via addition of vinylmagnesium bromide to a d-mannose-derived aldehyde, which forms the new C–N bond with complete regio- and stereocontrol according to the tethering approach. Subsequent intramolecular reductive amination afforded the desired azepanes. This method represents the first application of the osmium-catalyzed tethered aminohydroxylation reaction to the synthesis of iminosugars. American Chemical Society 2023-07-29 /pmc/articles/PMC10425973/ /pubmed/37515782 http://dx.doi.org/10.1021/acs.orglett.3c02087 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Martínez-Bailén, Macarena
Matassini, Camilla
Clemente, Francesca
Faggi, Cristina
Goti, Andrea
Cardona, Francesca
Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation
title Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation
title_full Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation
title_fullStr Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation
title_full_unstemmed Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation
title_short Stereoselective Synthesis of Heavily Hydroxylated Azepane Iminosugars via Osmium-Catalyzed Tethered Aminohydroxylation
title_sort stereoselective synthesis of heavily hydroxylated azepane iminosugars via osmium-catalyzed tethered aminohydroxylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10425973/
https://www.ncbi.nlm.nih.gov/pubmed/37515782
http://dx.doi.org/10.1021/acs.orglett.3c02087
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