Highly diastereoselective addition of alkoxyethynyl aluminum reagents to N-tert-butylsulfinyl aldimines.

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.

Références

Titre
Highly diastereoselective addition of alkoxyethynyl aluminum reagents to N-tert-butylsulfinyl aldimines.
Type de publication
Article de revue
Année de publication
2014
Revue
Org. Biomol. Chem.
Volume
12
Pagination
1875–1878
ISSN
1477-0520
Soumis le 12 avril 2018