Lithiation of 2-(1-Chloroethyl)-2-oxazolines: Synthesis of Substituted Oxazolinyloxiranes and Oxazolinylaziridines

Lithiation of 2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 2 leads to lithiated derivative 3, which is quite stable and can be deuterated, methylated and silylated to give oxazolines 4a-c. The reaction of 3 with carbonyl compounds and imines furnishes good to excellent yields of oxazolinylepoxides 6a-m and aziridines 17a-f, respectively. Methylation and NaBH 4 reduction of epoxides 6 afford oxazolidines 7 highly stereoselectively. Acylepoxides can be obtained by hydrolysis of the oxazolidine moiety.