Application of Redox-Active Ester Catalysis to the Synthesis of Pyranose Alkyl C‑Glycosides

The direct coupling of shelf-stable, tetrachloro-N-hydroxyphthalimide ester (TCNHPI) glycosyl donors with a variety of alkylzinc reagents under redox catalysis is described. Alkyl C-glycosides are formed directly by a decarboxylative, Negishi-type process in 31–73% yields without the need for photoc...

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Bibliographic Details
Published in:Organic letters 2023-05, Vol.25 (20), p.3760-3765
Main Authors: Romeo, Joseph R., Lucera, Jon D., Jensen, Drew, Davis, Luke M., Bennett, Clay S.
Format: Article
Language:English
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Summary:The direct coupling of shelf-stable, tetrachloro-N-hydroxyphthalimide ester (TCNHPI) glycosyl donors with a variety of alkylzinc reagents under redox catalysis is described. Alkyl C-glycosides are formed directly by a decarboxylative, Negishi-type process in 31–73% yields without the need for photocatalytic activation or additional reductants. Extension of this approach to the coupling of TCNHPI donors with stereodefined α-alkoxy furan-containing alkylzinc halides enabled de novo synthesis of methylene-linked exo-C-disaccharides via an Achmatowicz rearrangement.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01228