Département de chimie moléculaire

The addn. of dimethylaluminium (alkoxya)cetylide derivs. to Ellman's sulfinylimines is described. The reaction proceeds with excellent diastereoselectivity and high yield to produce oxygenated propargylamines in one step starting from simple dichloroenol ethers. Transmetalation of 2-[[(1E)-1,2-dichloroethenyl]oxy]-2-methylpropane, 1-[[(1E)-1,2-dichloroethenyl]oxy]-4-methoxybenzene gave [(alkoxy)ethynyl]aluminum derivs. (aluminum acetylide ethers). The synthesis of the target compds. was achieved by a reaction of [(alkoxy)ethynyl]aluminum derivs. (aluminum acetylide ethers) with [N(E),S(S)]-2-methyl-N-(phenylmethylene)-2-propanesulfinamide, [N(E)]-2-methyl-N-(phenylmethylene)-2-propanesulfinamide, [N(E)]-2-Methyl-N-(2-furanylmethylene)-2-propanesulfinamide, etc.