Progress toward improving the diastereoselectivity of the Meyers ortho-alkylation of chiral aromatic oxazolines

ORGN 87

Julianne McLaughlin, wyattj@cofc.edu, Jason S. Overby, overbyj@cofc.edu, and Justin K. Wyatt. Department of Chemistry and Biochemistry, College of Charleston, 66 George St, Charleston, SC 29424
Aromatic oxazolines are powerful compounds to introduce alkyl groups on an aromatic ring. Chiral applications of this process have shown to give good yields of the alkylated products but with only low to moderate diastereoselectivity. Improving the low diastereoselectivity of this methodology will be demonstrated using a chiral α,α-disubstituted amino acid as the basis for the chiral aromatic oxazolines formation. The improved chiral aromatic oxazoline rational and synthesis will be presented.