Diastereoselective access to C , C -glycosyl amino acids via iron-catalyzed, auxiliary-enabled MHAT coupling.

Autor: Lang M; Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France. philippe.compain@unistra.fr., Tardieu D; Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France. philippe.compain@unistra.fr., Pousse B; Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France. philippe.compain@unistra.fr., Compain P; Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France. philippe.compain@unistra.fr., Kern N; Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France. philippe.compain@unistra.fr.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Mar 14; Vol. 60 (23), pp. 3154-3157. Date of Electronic Publication: 2024 Mar 14.
DOI: 10.1039/d3cc06249j
Abstrakt: Access to C , C -glycosyl amino acids as a novel class of glycomimetics is reported by means of radical generation, intermolecular addition and stereoselective reduction via a metal-induced hydrogen atom transfer (MHAT) sequence. The 'matched' coupling of exo -D-glycals with an enantiopure dehydroalanine bearing a ( R )-configured benzyl oxazolidinone enables a singular case of two-fold diastereocontrol under iron catalysis. In the common exo -D-glucal series, the nature of the C-2 substituent was found to play a key role from both reactivity and stereocontrol aspects.
Databáze: MEDLINE
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