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

The reaction of chiral (2R,1‘S)- or (2S,1‘S)-2-(1-aminoalkyl)epoxides 1 or 2 with CO2, generated from acidic treatment of an aqueous solution of NaHCO3 at room temperature, efficiently afforded enantiopure cyclic carbonates 3 or 4, respectively, with total selectivity. Compounds 3 and 4 were readily transformed into the corresponding diols 7 and 8 by reaction with LiAlH4 or by basic hydrolysis. When compounds 3 or 4 were allowed to react with methyllithium at −78 °C, O1-acetylalkane-1,2-diols 9 and 10 were obtained with total or high selectivity.