Reagent- and chelation-controlled diastereoselective aziridination of electron-rich alkenes by 3-acetoxyamino-2-(1-hydroxy-2,2-dimethylprop-1-yl)-quinazolin-4(3H)-one

Abstract

In the presence of titanium (IV)tert-butoxide, the title 3-acetoxyaminoquinazolinone aziridinates styrene, butadiene and indene completely diastereoselectively; the absolute configuration of the styrene-derived aziridine 6a is proven by X-ray crystallography and is consistent with a transition state model involving chelation control by titanium.