Stereoselective Synthesis of Glycosides via Tsuji–Trost Type Glycosylation Using 3,4‐Carbonate Galactals

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Abstract: Pd‐catalyzed stereoselective glycosylations using unsaturated sugar derivatives, glycals, have been successfully achieved in recent years. This review focuses on approaches to control the stereoselectivities of glycosides via π‐allyl intermediates that mimic the Tsuji–Trost asymmetric allylic alkylation reactions, enabling stereoselectivity control through rational design. In the reaction process, zwitterionic Pd‐π‐allyl complexes, formed after the oxidative addition and decarboxylation, play a crucial role in increasing reactivities and enhancing the stereoselectivities of α‐ and β‐glycosides. We summarized recently developed Tsuji–Trost type glycosylations using 3,4‐carbonate galactals, featuring high efficiency, exclusive stereoselectivities, and a broad reaction scope including O‐, N‐, S‐, and C‐glycosylations.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereoselective Synthesis of Glycosides via Tsuji–Trost Type Glycosylation Using 3,4‐Carbonate Galactals ; day:21 ; month:08 ; year:2024 ; extent:13
The chemical record ; (21.08.2024) (gesamt 13)

Creator: Kim, Ye Lim
Kim, Ju Hyun

DOI: 10.1002/tcr.202400067

URN: urn:nbn:de:101:1-2408211440483.534594325436

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:00 AM CEST

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Kim, Ye Lim
Kim, Ju Hyun

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Stereoselective Synthesis of Glycosides via Tsuji–Trost Type Glycosylation Using 3,4‐Carbonate Galactals

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