Totally Selective Reaction of CO₂ with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1'S)- or (4S,1'S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes

José M. Concellón*, Virginia del Solar, Santiago García-Granda and M. Rosario Díaz

*Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, V. del Solar, S. Carcía-Granda, M. R. Díaz, J. Org. Chem., 2007, 72, 7567-7568.

DOI: 10.1021/jo070829x

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Abstract

The reaction of chiral 1-aminoalkylepoxides with CO₂, generated from acidic treatment of an aqueous solution of NaHCO₃ at room temperature, efficiently afforded enantiopure cyclic carbonates with total selectivity. Carbonates were readily transformed into the corresponding diols by reaction with LiAlH₄ or by basic hydrolysis.

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Key Words

dioxolanones, diols, cleavage of carbonates, esters

ID: J42-Y2007-3050

Totally Selective Reaction of CO2 with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1'S)- or (4S,1'S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes

José M. Concellón*, Virginia del Solar, Santiago García-Granda and M. Rosario Díaz

Totally Selective Reaction of CO₂ with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1'S)- or (4S,1'S)-4-(1-Aminoalkyl)-2-oxo-1,3-dioxolanes