The reaction of chiral (2
R,1'
S)- or (2
S,1'
S)-2-(1-a
minoalkyl)epoxides
1 or
2 with CO
2, generated fro
macidic treat
ment of an aqueous solution of NaHCO
3 at roo
m te
mperature, efficiently afforded enantiopurecyclic carbonates
3 or
4, respectively, with total selectivity. Co
mpounds
3 and
4 were readily transfor
medinto the corresponding diols
7 and
8 by reaction with LiAlH
4 or by basic hydrolysis. When co
mpounds
3 or
4 were allowed to react with
methyllithiu
m at -78 C,
O1-acetylalkane-1,2-diols
9 and
10 wereobtained with total or high selectivity.