1-Iodoglycal: A Versatile Intermediate for the Synthesis of d-Glyco Amides and Esters Employing Carbonylative Cross-Coupling Reaction.
Milene M HorninkMonica F Z J ToledoDaniel Carvalho PimentaCaio PaschoalinPamela M SilvaGiuseppe E FiglinoEurípedes AguiarGustavo CerviFrancisco W M RibeiroThiago Carita CorreraAngélique FerryHélio A StefaniPublished in: ACS omega (2024)
In this study, we present the development of two catalytic processes: a Pd-PEPPSI-catalyzed aminocarbonylation and a Pd(OAc) 2 -Xantphos-catalyzed alkoxycarbonylation of d-glycals, utilizing carbonylative cross-coupling reactions. We explored successfully various types of aromatic amines, as well as alkyl amines and amino acids, to synthesize new d-glycal amides. However, we observed limitations in the reactivity of alkyl and heteroaromatic amines. The processes enabled the synthesis of 20 novel C1-branched glycoamides and 7 new d-gluco esters.
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