ORGN 759 |
Propargyl amides are cyclized in a one-pot operation yielding 2-bromomethyl oxazoles. Gold trichloride catalyzes the formation of an intermediate exocyclic enol ether, which is trapped with bromine to give the desired compound in a one-pot operation. 2-Bromomethyl oxazoles have proven to be a versatile intermediate, giving access to dipeptide isosteres, bis-heterocycles, acetates, ethers, and amines in 3-4 steps from commercially available starting materials. |
Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |