Catalytic oxidative carbonylation of aminoalcohols

ORGN 451

Delmy J. Díaz, delmydiaz@yahoo.com and Lisa McElwee-White, lmwhite@chem.ufl.edu. Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200
Aminoalcohols undergo W(CO)6-catalyzed oxidative carbonylation to the corresponding hydroxyalkylureas without protection of the hydroxyl group. Selected examples of 1,2-, 1,3-, 1,4- and 1,5-aminoalcohols were converted to the ureas in good to excellent yields, with only small amounts of the cyclic carbamates being formed. In contrast, stoichiometric reactions of the phosgene derivatives 1,1'-carbonyldiimidazole (CDI) and S,S'-dimethyl dithiocarbonate (DMDTC) with 1,3- and 1,2-aminoalcohol substrates exhibit variable selectivities between ureas and cyclic carbamates

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006