Synthesis and applications of 2-bromomethyl oxazoles

ORGN 759

Christopher L. Paradise, christopher.paradise@utsouthwestern.edu, Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Blvd, Dallas, TX 75390, Pooja Sarkar, Cornell University, and Jef K. De Brabander, jdebra@biochem.swmed.edu, Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, Dallas, TX 75390.
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.