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 lithiat ed derivative 3, which is quite stable and can be deuterated, methylated an d silylated to give oxazolines 4a-c. The reaction of 3 with carbonyl compou nds and imines furnishes good to excellent yields of oxazolinylepoxides 6a- m and aziridines 17a-f, respectively . Methylation and NaBH4 reduction of e poxides 6 afford oxazolidines 7 highly stereoselectively. Acylepoxides can be obtained by hydrolysis of the oxazolidine moiety.