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Updated: Jul 2, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Diastereoselective access to C,C-glycosyl amino acids via iron-catalyzed, auxiliary-enabled MHAT coupling
Mylène Lang1, Damien Tardieu1, Benoit Pousse1
1Laboratoire 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.
Abstract:
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.
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