title: Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.
abstract: We describe highly enantioselective synthesis of beta-amino acid derivatives (1a-c) using asymmetric hydrogenation of alpha-aminomethylacrylates (2a-c), which contain a free basic N H group, as the key step. The alpha-aminomethylacrylates (2a-c) were prepared using the Baylis-Hillman reaction of an appropriate aldehyde with methyl acrylate followed by acetylation of the resulting allylic alcohols (4a-b) and S(N)2'-type amination of the allylic acetates (3a-b).
authors.affiliation: Process Research and Development, Chemical and Analytical Development, Novartis Pharmaceuticals Corporation, One Health Plaza, East Hanover, NJ 07936, USA.
authors.forename: Liqin
authors.initials: L
authors.lastname: Qiu
authors.forename: Mahavir
authors.initials: M
authors.lastname: Prashad
authors.forename: Bin
authors.initials: B
authors.lastname: Hu
authors.forename: Kapa
authors.initials: K
authors.lastname: Prasad
authors.forename: Oljan
authors.initials: O
authors.lastname: Repic
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Blacklock
authors.forename: Fuk Yee
authors.initials: FY
authors.lastname: Kwong
authors.forename: Stanton H L
authors.initials: SH
authors.lastname: Kok
authors.forename: Hang Wai
authors.initials: HW
authors.lastname: Lee
authors.forename: Albert S C
authors.initials: AS
authors.lastname: Chan
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D006865:Hydrogenation; D008689:Methacrylates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D008689:Methacrylates