Reduction of O-methyl oxime ethers of conjugated cyclohexenones with aluminum hydride

The reduction of representative O-methyl oxime ethers 1–4 with aluminum hydride in tetrahydrofuran yielded allylic amines and saturated aziridines as the main products. The stereochemical course of the reduction to aziridines depends on the oxime ether configuration. Thus, E–3, E–4 and Z–3, Z–4 gave 15, 16 and 21, 22 , respectively, with high stereoselectivity. Higher reactivity of Z than E isomers was utilized for the preparation of pure E isomers of oxime ethers from E, Z mixtures.