1‑Iodoglycal: a versatile intermediate for the synthesis of d‑glyco amides and esters employing carbonylative cross-coupling reaction

Abstract

In this study, we present the development of two catalytic processes: a Pd-PEPPSI-catalyzed aminocarbonylation anda Pd(OAc)2-Xantphos-catalyzed alkoxycarbonylation of D-glycals, utilizing carbonylative cross-coupling reactions. We exploredsuccessfully 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.