Hypervalent Chalcogenonium H-Bonding Organocatalysis for the Direct Stereoselective Synthesis of Deoxyglycosides
Year: 2025
Type: preprint
Abstract: The use of trisubstituted selenonium salts as organocatalysts for the direct and stereoselective synthesis of deoxyglycosides from hemiacetals is described. The reaction conditions are mild and compatible with various functionalities and has a broad substrate scope including examples of 1-hydroxy deoxy-galactoside and glucoside substrates. Mechanistic investigations suggest that the reaction proceeds via a step-wise process involving the he hemiacetal donor, OH acceptor and catalyst, whereby the chalcogen catalysts mediates the key H+ transfer step. This study opens a new avenue for the development of nonmetallic acid/base catalysis for the stereoselective synthesis of complex glycosides.
Source: ChemRxiv
Authors: Jennifer Johns, Mukul Mahanti, Thomas Hansen, M. Carmen Galan
Institution: University of Bristol
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Award: G5558554490
OpenAlex ID: W4409458971