A stereospecific synthesis of vicinal amino alcohols by aminolysis of vinylepoxides

Autor: Lindström, Ulf M., Franckowiak, Remi, Pinault, Nathalie, Somfai, Peter
Zdroj: Tetrahedron Letters; January 1997, Vol. 38 Issue: 11 p2027-2030, 4p
Abstrakt: Several vinylepoxides have been prepared and subjected to a TsOH·H 2O-catalyzed aminolysis reaction to afford the corresponding amino alcohols in good yields. The nucleophilic addition is stereospecific and proceeds with high regioselectivity at the allylic position, unless other stereoelectronic effects competes. The aminolysis reaction is sensitive to steric hindrance at or in the proximity of the oxirane nuclei.
Databáze: Supplemental Index