title: Enantiocontrolled synthesis of alpha-methyl amino acids via Bn2N-alpha-methylserine-beta-lactone.
abstract: [Reaction: see text] Enantiocontrolled synthesis of alpha-methyl amino acids proceeds via the regioselective organocuprate opening of Bn2N-alpha-methylserine-beta-lactone. From this chiral intermediate, a wide variety of alpha-methyl amino acids and building blocks were synthesized in excellent yields.
authors.affiliation: Department of Chemistry, University of California, San Diego, La Jolla, California 92093, USA. smithn@uchicago.edu
authors.forename: Nicole D
authors.initials: ND
authors.lastname: Smith
authors.forename: Aaron M
authors.initials: AM
authors.lastname: Wohlrab
authors.forename: Murray
authors.initials: M
authors.lastname: Goodman
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008697:Methane / Q000737:chemistry*; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007783:Lactones; C476502:alpha-methyl-D-serine-beta-lactone; D012694:Serine; D008697:Methane