Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.
A variety of heterocyclic alcohols and acetates were coupled with silyl ketene acetals and other π-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array of substituted β-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the π-nucleophile bears a chiral auxiliary.
Fu
Tsung-Hao
TH
Department of Chemistry and Biochemistry, The University of Texas, Austin, TX USA 78712.
Bonaparte
Amy
A
Martin
Stephen F
SF