Organo-zinc Promoted Diastereoselective C‑Arylation of 1,2-Anhydrosugars from Arylboronic Acids

α-C-arylglycosides can be obtained through the addition of aryl zinc reagents to sugar epoxides. The required aryl zinc nucleophiles can be easily obtained from the corresponding boronic acids by B–Zn exchange and attack sugar 1,2 epoxides in a highly diastereoselective fashion to generate 1,2-cis-α...

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Veröffentlicht in:Organic letters 2015-09, Vol.17 (18), p.4624-4627
Hauptverfasser: Tatina, Madhu Babu, Kusunuru, Anil Kumar, Mukherjee, Debaraj
Format: Artikel
Sprache:eng
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Zusammenfassung:α-C-arylglycosides can be obtained through the addition of aryl zinc reagents to sugar epoxides. The required aryl zinc nucleophiles can be easily obtained from the corresponding boronic acids by B–Zn exchange and attack sugar 1,2 epoxides in a highly diastereoselective fashion to generate 1,2-cis-α-hexapyranosyl aryl glycosides under ligand- and base-free conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02364