title: A one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids.
abstract: The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-L-pipecolic acids using a tandem reductive amination/6-endo-trig cyclisation process is described. The sequential reduction and cyclisation mediated by sodium cyanoborohydride allowed the preparation of a series of highly functionalised 6-alkyl and 6-aryl analogues.
authors.affiliation: WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow, G12 8QQ, UK.
authors.forename: Lindsay S
authors.initials: LS
authors.lastname: Fowler
authors.forename: Lynne H
authors.initials: LH
authors.lastname: Thomas
authors.forename: David
authors.initials: D
authors.lastname: Ellis
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D000586:Amination; D001894:Borohydrides / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010875:Pipecolic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001894:Borohydrides; D010875:Pipecolic Acids; C009282:sodium cyanoborohydride; C031345:pipecolic acid