Acetic acid aldol reactions in the presence of trimethylsilyl trifluoromethanesulfonate.

N-Trimethylsilyloxy-enamines as New Aldehyde Enolate Synthons: General, Efficient and Diastereoselective Aldol Reaction with Ketals and Acetals Induced by Trimethylsilyl Trifluoromethanesulfonate

Rapid oxidation of alcohols and trimethylsilyl and tetrahydropyranyl ethers with CrO3 in the presence of sulfonic acid functionalized ordered nanoporous Na+-montmorillonite

A mild, efficient and fast method for the oxidation of alcohols and trimethylsilyl and tetrahydropyranyl ethers to their corresponding carbonyl compounds using CrO3 in the presence of sulfonic acid functionalized ordered nanoporous Na+-montmorillonite (SANM) and under solvent-free conditions is reported. All reactions were performed at room temperature in high to excellent...

Rapid oxidation of alcohols and trimethylsilyl and tetrahydropyranyl ethers with CrO3 in the presence of sulfonic acid functionalized ordered nanoporous Na+-montmorillonite

A mild, efficient and fast method for the oxidation of alcohols and trimethylsilyl and tetrahydropyranyl ethers to their corresponding carbonyl compounds using CrO3 in the presence of sulfonic acid functionalized ordered nanoporous Na+-montmorillonite (SANM) and under solvent-free conditions is reported. All reactions were performed at room temperature in high to excellent...

Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations

The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

A Tandem Enol Silane Formation-Mukaiyama Aldol Reaction Mediated by TMSOTf

A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation-Mukaiyama aldol reaction in the presence of Hunig’s base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75-97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for f...