Cu(I)-NHC catalyzed asymmetric silyl transfer to unsaturated lactams and amides.

The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe2SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.

NHC-Cu(I) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution.

The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric NHC-Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones. The method has been exploited in an expedient synthesis of (+)-blastmycinone.