“CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2‑Iodoglycals

“CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2‑Iodoglycals

Development of a palladium-catalyzed carbonylative Suzuki–Miyaura coupling reaction between 2-iodoglycal partners and diverse aryl- and alkenyl-boronic acids is presented, leading to original 2-ketoglycals. The newly formed carbonyl link could be exploited to access 2-aryl/alkenyl-methylene-α-glucop...

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Veröffentlicht in:Journal of organic chemistry 2019-03, Vol.84 (6), p.3328-3339
Hauptverfasser: de Robichon, Morgane, Bordessa, Andrea, Lubin-Germain, Nadège, Ferry, Angélique
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
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Zusammenfassung:Development of a palladium-catalyzed carbonylative Suzuki–Miyaura coupling reaction between 2-iodoglycal partners and diverse aryl- and alkenyl-boronic acids is presented, leading to original 2-ketoglycals. The newly formed carbonyl link could be exploited to access 2-aryl/alkenyl-methylene-α-glucopyranoside scaffolds via a three-step sequence including an indium-mediated Ferrier-type reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03248