Synthesis of a tertiary carbinamide via a novel Rh-catalyzed asymmetric hydrogenation

[GRAPHICS] Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(1)-Josiphos complex in THF under 500 psi of H(2) generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio.