212072-14-5

Upstream product

• 676-58-4 methylmagnesium chloride 
• 119-61-9 benzophenone 
• 73470-71-0 2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 
• 212071-84-6 2-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxy-1,1-diphenylpropane 
• 181038-11-9 1-(4,4-dimethyl-2-oxazolin-2-yl)-1,2-epoxy-2,2-diphenylethane 

Downstream Products

• 23457-03-6 3,4-epoxy-3-methyl-4,4-diphenylbutan-2-one 
• 23457-06-9 3,3-diphenylpentane-2,4-dione 

Relevant academic research and scientific papers

An efficient synthesis of oxiranyl oxazolines and elaboration to acyl oxiranes

Deprotonation of oxazolinyl oxirane 1a with sec-BuLi/TMEDA at -100 °C in Et20 furnished oxazolinyl oxiranyllithium 1b, which could be trapped with electrophiles to give oxiranes 1c-g. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-oxazolinyl-2-p-tolyl epoxy ethane 1h was found to be configurationally stable while oxiranyllithium 1I, generated from the cis isomer 1k, was not. Oxazolinyl epoxides 1d, 1j and 1m could be deblocked to acyl oxiranes 5a-e through oxazolidines 4a-e.

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 NaBH4 reduction of epoxides 6 afford oxazolidines 7 highly stereoselectively. Acylepoxides can be obtained by hydrolysis of the oxazolidine moiety.