Preparation of N–H azirdines in high enantiomeric excess by in situ aziridine–azirine–aziridine interconversion
Abstract
Aziridine 6 is produced highly diastereoselectively by treatment of enantiopure 3-acetoxyaminoquinazolinone 4(Q*NHOAc) with β-trimethylsilylstyren:desilylative elemination of Q* and in situ addition fo cyanide to the intermediate azirine gives the NH-aziridine 8 of 83% ee.