Enantiomerically pure 2-alkyl and 2,3-dialkylaziridines from 2-sulfinylimines

✍ Scribed by JoséL. García Ruano; Antonio Lorente; Jesús H. Rodríguez Ramos

• Book ID: 104260305
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 269 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02168-6

✦ Synopsis

A new entry to optically pure aziridines from N-p-methoxyphenyl derivatives of 2-p-tolylsulfinylketimines is reported. The highly stereoselective reduction of the imines with DIBAL-H/ZnX2 yielded the corresponding sulfinyl amines, which can be transformed into the N-Cbz derivatives through a two-step sequence involving reaction with BnO2CCI and subsequent oxidation with CAN. These compounds were easily transformed into optically pure aziridines by reduction of the sulfinyl group, further methylation at sulfur, and final cyclization with base.