Cycloadditions to pyrimidines promoted by tungsten

ORGN 450

Yogesh Surendranath, yogeshs@mit.edu, Department of Chemistry, Nocera Group, Massachusetts Institute of Technology, 2-301, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139-4307 and W. Dean Harman, Department of Chemistry, University of Virginia, Charlottesville, VA 22903.
Pyrimidines exhibit facile η1 to η2 isomerization when coordinated to the π-basic metal fragment, {TpW(NO)(PMe3)} (Tp = hydridotris(pyrazolyl)borate). Metal coordination promotes the pyrimidine towards Diels-Alder cycloaddition to produce [2.2.2]diazabicyclooctadienes. Cycloaddition proceeds regioselectively with the dienophile withdrawing group orienting anti to the pyrimidine nitrogens.

 

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