Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
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چکیده
منابع مشابه
Palladium‐Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals
Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nu...
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Pd(MeCN)2Cl2 enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to preactivate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxy...
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A fast and convenient synthesis of arylamidines starting from readily available potassium aryltrifluoroborates and cyanamides is reported. The coupling was achieved by Pd(II)-catalysis in a one step 20 min microwave protocol using Pd(O(2)CCF(3)), 6-methyl-2,2'-bipyridyl, TFA, and MeOH, providing the corresponding arylamidines in moderate to excellent yields.
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The flexible installations of a sulfamate ester on a glycal scaffold at C3, C4, or C6 approaching alpha- or beta-aminoglycosides is communicated. A variety of glycal acceptors (O, S, and N) were applied, enhancing the utility of this method as an operationally simple protocol for the stereoselective synthesis of polyfunctionalized alpha- or beta- aminosaccharides.
متن کاملTMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.
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ژورنال
عنوان ژورنال: Angewandte Chemie
سال: 2017
ISSN: 0044-8249
DOI: 10.1002/ange.201612071