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

[GRAPHICS] 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 degrees C, O-1-acetylalkane-1,2-diols 9 and 10 were obtained with total or high selectivity.