212072-13-4Relevant academic research and scientific papers
Lithiation of 2-(1-chloroethyl)-2-oxazolines: Synthesis of substituted oxazolinyloxiranes and oxazolinylaziridines
Capriati,Degennaro,Florio,Luisi,Tralli,Troisi
, p. 2299 - 2306 (2007/10/03)
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.
Deprotonation of oxazolinyloxiranes: Formation of substituted acyloxiranes
Florio, Saverio,Capriati, Vito,Di Martino, Serena,Abbotto, Alessandro
, p. 409 - 417 (2007/10/03)
Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at - 100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds 1b, 1i, and 1I which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxy-ethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.
An efficient synthesis of oxiranyl oxazolines and elaboration to acyl oxiranes
Florio, Saverio,Capriati, Vito,Di Martino, Serena
, p. 5639 - 5642 (2007/10/03)
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.
