Synthesis of Acetonides from Epoxides Catalyzed by Erbium(III) Triflate

Abstract

Epoxides dissolved in acetone can be converted almost quantitatively in acetonides in the presence of catalytic amounts of erbium(III) triflate. The procedure can be usefully applied to other substrates and can be extended to other ketones.

Regioselective Ring‐Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]‐FeIII Triflate Complex

“…The reactionp roceeded with high activity (initial turnover frequency of 1680 h À1 for EtOH) and selectivity( > 95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in ar egioselective fashion (84-96 %y ield of the non-symmetric regioisomer). [12][13][14] We have recentlys hown that GLYc an be conveniently obtained as a value-added product from biobasedepichlorohydrin (ECH) productionp lants (EPICEROL process, Solvay), [15] thereby enhancing the environmental sustainability of the entireE CH chain as well as interest towards GLYc onversiont ov aluable chemicals such as polymers, [16] drugs, [17] diols, [18][19][20] solketal, [21,22] and organic carbonates. [1][2][3][4][5][6][7] In particular, since the discoveryo fm anyu seful synthetic strategies that have given access to aw ide variety of chiral epoxides, this reaction has becomeani mportant entry in the toolbox of organic synthesis for obtaining enantiopure molecules.…”

“…[1][2][3][4][5][6][7] In particular, since the discoveryo fm anyu seful synthetic strategies that have given access to aw ide variety of chiral epoxides, this reaction has becomeani mportant entry in the toolbox of organic synthesis for obtaining enantiopure molecules. [12][13][14] We have recentlys hown that GLYc an be conveniently obtained as a value-added product from biobasedepichlorohydrin (ECH) productionp lants (EPICEROL process, Solvay), [15] thereby enhancing the environmental sustainability of the entireE CH chain as well as interest towards GLYc onversiont ov aluable chemicals such as polymers, [16] drugs, [17] diols, [18][19][20] solketal, [21,22] and organic carbonates. [12][13][14] We have recentlys hown that GLYc an be conveniently obtained as a value-added product from biobasedepichlorohydrin (ECH) productionp lants (EPICEROL process, Solvay), [15] thereby enhancing the environmental sustainability of the entireE CH chain as well as interest towards GLYc onversiont ov aluable chemicals such as polymers, [16] drugs, [17] diols, [18][19][20] solketal, [21,22] and organic carbonates.…”

Transacetalization of Solketal: A Greener Route to Bioglycerol‐Based Speciality Chemicals

“…Acetals and ketals of glycerol are obtained via direct acid‐catalyzed condensation of glycerol with carbonyl compounds, via transacetalization of glycerol by corresponding dimethylacetals, or through addition of carbonyl compounds to glycidol in the presence of Lewis acids (Scheme ). For the direct acetalization starting from glycerol and carbonyl compounds both homogeneous (sulfuric acid,, p‐TSA, sulfonated polyvinyl alcohol, Fe(III) and Sn(II)salts) and heterogeneous acid catalysts (the most promising for the industrial application here are zeolites, and sulfonic ion‐exchange resins,,,).…”

Efficient and Selective Acetylation of Biomolecules with 1-Acetylimidazole Catalyzed by Er(OTf)_3.

“…Considering the stability and catalytic activity of Erbium (III) in water that can be ascribed to their large ionic radii and an equilibrium between the Lewis acids and water [26] and taking into account our experience in developing eco-friendly reactions [27] and selective procedures for the protection of natural compounds, [28][29][30][31][32][33][34] we decided to test the reactivity of 1-acetylimidazole and the catalytic activity of Er(OTf)3 in water for the selective acetylation of bioactive compounds.…”