Palladium-catalyzed stereoselective formation of α-O-glycosides

Organic Letters

Volumn 9, Issue 16, 2007, Pages 3173-3176

  Schuff, Brandon P ^a   Mercer, Gregory J ^a   Nguyen, Hien M ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; GLYCOSIDES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 34547962691     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071268z     Document Type: Article

References (21)

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18. 3 and DTTBP in the presence of 1-naphthol only gave 26% yield of 5 with α/β = 1.5:1. This result suggests that our method may not go through Pd(0).
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21. A similar glycosylation was reported by Schmidt and coworkers utilizing TMSOTf as a Lewis acid to catalyze the reaction of 18 with alipahtic alcohol acceptors: Abdel-Rahman, A. A.-H.; Winterfield, G. A.; Takhi, M.; Schmidt, R. R. Eur. J. Org. Chem. 2002, 713-717. Our question is whether the Lewis-acid catalyzed Ferner reaction is applicable to a variety of glycal imidates and aryl/alkyl alcohols acceptors. Under Schmidt's conditions, treatment of 4 with 5 mol% of TMSOTf and 1.1 equiv of 1-naphthol or benzyl 2,3-O-isopropylidene-D-ribosefuranoside only resulted in multiple products.