Aziridination of cyclohex-2-enols and 3-substituted cyclohexenes: comparison with epoxidation

Abstract

Aziridination of cyclohex-2-enol, 3-methylcyclohex-2-enol, and 3-phenylcyclohex-2-enol with 3-acetoxyamino-2-ethylquinazolin-4(3H)-one (4) proceeds with high stereoselectivity syn to the hydroxy group to give compounds (7), (19), and (21), respectively in good yields. These results are analogous to the epoxidations of these alkenes using peracids. Aziridinations of cyclohex-2-enyl acetate or cyclohex-2-enyl methyl ether proceed stereospecifically anti to the acetoxy or methoxy group to give (11) and (17), respectively, but in low yield. These results are in contrast to the epoxidations of these alkenes using peracids.

The configurations assigned to these products are supported by an analysis of the n.m.r. spectra of 2-substituted 7-azabicyclo[4.1.0] heptanes.