Selective functionalization of cyano-phenyl-2-oxazolines using TMPMgCl center dot LiCl

Metalated phenyl-2-oxazolines bearing cyano groups can be selectively obtained through the reaction of TMPMgCl center dot LiCl with the appropriate substrate. Subsequent reaction with different electrophiles furnished the functionalized derivatives in good yields. Density functional theory (DFT) calculations were performed to evaluate the influence of the ring substituents on the acidity of the aromatic hydrogens. Application to the synthesis of novel functionalized phthalides illustrates the great potential of the methodology to the synthesis of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved. (AU)