title: Asymmetric Reduction of Lactam-Based β-Aminoacrylates. Synthesis of Heterocyclic β(2)-Amino Acids.
abstract: The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1-3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β(2)-amino acids 3b and 5b with high enantioselectivity (≥97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.
authors: School of Chemistry, University of Bristol , Bristol BS8 1TS U.K.
authors: Hugo Rego
authors: HR
authors: Campello
authors: AstraZeneca , Pharmaceutical Development, Silk Road Business Park, Macclesfield SK10 2NA U.K.
authors: Jeremy
authors: J
authors: Parker
authors: AstraZeneca , Innovative Medicines, R&I Chemistry, AstraZeneca R&D Mölndal, Peparedsleden, SE-431 83 Mölndal, Sweden.
authors: Matthew
authors: M
authors: Perry
authors: AstraZeneca , PR&D Södertälje, S-151 85 Södertälje, Sweden.
authors: Per
authors: P
authors: Ryberg
authors: School of Chemistry, University of Bristol , Bristol BS8 1TS U.K.
authors: Timothy
authors: T
authors: Gallagher
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000179:Acrylates; D000596:Amino Acids; D006571:Heterocyclic Compounds; D007769:Lactams