Reaction of Tributyltin Hydride with α,β-Unsaturated N-Acyloxazolidinones

The treatment of tributyltin hydride with α-substituted propenoyl oxazolidinones in the presence of a catalytic amount of AIBN gave the tributyltin radical addition adduct when the substituent is an alkyl group. However, when the substituent is an aryl group, the reduction adduct was obtained in modest diastereoselectivity. The yield of this reduction process was improved by using Pd(PPh₃)₄ as a catalyst. The application of this stereoselective hydrogenation reaction to the synthesis of α-alkyl arylacetic acids is described.

stereoselective hydrogenation - α-alkyl arylacetic acids - tributyltin hydride - N-(α-phenylacryloyl)oxazolidinone