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
- Auteurs
- Verrier, Charlie, Carret Sébastien, and Poisson Jean-François
- Revue
- Org. Biomol. Chem.
- Volume
- 12
- Pagination
- 1875–1878
- ISSN
- 1477-0520
Soumis le 12 avril 2018