Stereoselective Synthesis of Glycosides via Tsuji-Trost Type Glycosylation Using 3,4-Carbonate Galactals.
Chem Rec
; : e202400067, 2024 Aug 21.
Article
en En
| MEDLINE
| ID: mdl-39166700
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 ß-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.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chem Rec
Asunto de la revista:
QUIMICA
Año:
2024
Tipo del documento:
Article
Pais de publicación:
Estados Unidos