Synthesis of Sugar-Based Enones and Their Transformation into 3,5-Disubstituted Furans and 2-Acyl-Substituted 1,2,3-Trideoxy Sugars in the Presence of Lewis Acids

• DOI: 10.1021/acs.orglett.9b00680
• Publication Date: 2019-04-19T20:40:50Z
• Authors: Nazar Hussain; Monika Bhardwaj; Ajaz Ahmed; Debaraj Mukherjee
• Keywords: Furan; Derivative (finance)

Pd-catalyzed carbonylative cross-coupling reactions of 2-iodoglycals have been developed for the synthesis sugar-based arylones and ynones using formic acid as carbonyl source. Whereas acetyl-protected lead to formation highly substituted furan derivatives in presence Lewis acid, benzyl-protected furnished 3-deoxy sugar derivative. In nucleophiles, an attack took place on C-1 or C-3 carbon regio- stereoselectively depending nature nucleophiles.