Aziridination of styrene derivatives with 3-acetoxyaminoquinazolinones: Probing transition state geometry from changes in diastereoselectivity

Article abstract of DOI:10.1016/S0040-4039(98)00939-3

In aziridinations of β-substituted styrenes (4), (5) and (6) with the enantiopure 3-acetoxy-aminoquinazolinone (1), diastereoselectivity (dr) increases from 5:1 (for (9) to 10:1 (for 10) for ~20:1 (for (11)): changes in transition state geometry which account for this increase are rationalised using Frontier Orbital Theory.