title: Highly diastereoselective heterogeneously catalyzed hydrogenation of enamines for the synthesis of chiral beta-amino acid derivatives.
abstract: Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.
authors.affiliation: Department of Process Research and the Catalysis and Reaction Discovery and Development Lab, Merck and Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. norihiro_ikemoto@merck.com
authors.forename: Norihiro
authors.initials: N
authors.lastname: Ikemoto
authors.forename: David M
authors.initials: DM
authors.lastname: Tellers
authors.forename: Spencer D
authors.initials: SD
authors.lastname: Dreher
authors.forename: Jinchu
authors.initials: J
authors.lastname: Liu
authors.forename: Angie
authors.initials: A
authors.lastname: Huang
authors.forename: Nelo R
authors.initials: NR
authors.lastname: Rivera
authors.forename: Eugenia
authors.initials: E
authors.lastname: Njolito
authors.forename: Yi
authors.initials: Y
authors.lastname: Hsiao
authors.forename: J Christopher
authors.initials: JC
authors.lastname: McWilliams
authors.forename: J Michael
authors.initials: JM
authors.lastname: Williams
authors.forename: Joseph D
authors.initials: JD
authors.lastname: Armstrong
authors.forename: Yongkui
authors.initials: Y
authors.lastname: Sun
authors.forename: David J
authors.initials: DJ
authors.lastname: Mathre
authors.forename: Edward J J
authors.initials: EJ
authors.lastname: Grabowski
authors.forename: Richard D
authors.initials: RD
authors.lastname: Tillyer
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003903:Deuterium; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006865:Hydrogenation; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000588:Amines; D000596:Amino Acids; D004952:Esters; D003903:Deuterium