title: Asymmetric Strecker synthesis of α-arylglycines.
abstract: A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure α-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4-methoxyphenyl)ethylamine affords highly crystalline (S,S)-α-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-α-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-α-arylglycines. The enantiopurities of these (S)-α-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by (1)H NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Pérez-Fuertes
authors.forename: James E
authors.initials: JE
authors.lastname: Taylor
authors.forename: David A
authors.initials: DA
authors.lastname: Tickell
authors.forename: Mary F
authors.initials: MF
authors.lastname: Mahon
authors.forename: Steven D
authors.initials: SD
authors.lastname: Bull
authors.forename: Tony D
authors.initials: TD
authors.lastname: James
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D004952:Esters; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C532809:2-formylphenylboronic acid; D001547:Benzaldehydes; D001897:Boronic Acids; D004952:Esters; D005998:Glycine