title: Synthesis of a tertiary carbinamide via a novel Rh-catalyzed asymmetric hydrogenation.
abstract: Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(I)-Josiphos complex in THF under 500 psi of H2 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.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, USA. john_limanto@merck.com
authors.forename: John
authors.initials: J
authors.lastname: Limanto
authors.forename: C Scott
authors.initials: CS
authors.lastname: Shultz
authors.forename: Benjamin
authors.initials: B
authors.lastname: Dorner
authors.forename: Richard A
authors.initials: RA
authors.lastname: Desmond
authors.forename: Paul N
authors.initials: PN
authors.lastname: Devine
authors.forename: Shane W
authors.initials: SW
authors.lastname: Krska
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003460:Crystallization; D006859:Hydrogen / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012211:Rhenium / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
chemical_list: D000577:Amides; D012211:Rhenium; D006859:Hydrogen