Reagent-controlled diastereoselectivity in aziridination of alkenes by chiral 3-acetoxyamino-3,4-dihydroquinazolin-4-ones: 1'-(t- butyldimethylsilyloxy)ethyl as the chiral 2-substituent on the quinazolinone

Article abstract of DOI:10.1016/0040-4039(96)01055-6

Conformational preferences within the (t)BuMe₂SiOCH(Me)C=N unit in 3- acetoxyaminoquinazolinone 3 lead to well defined site preferences for H, Me and OSiMe₂¹Bu in the transition state for, and hence high diastereoselectivity in, its reaction with β-trimethylsilylstyrene 4 to give aziridine 5.