title: Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.
abstract: A stereocontrolled synthesis of α-amino-α'-alkoxy ketones is described. This pH-neutral copper(I) thiophene-2-carboxylate (CuTC)-catalyzed cross-coupling of amino acid thiol esters and chiral nonracemic α-alkoxyalkylstannanes gives α-amino-α'-alkoxy ketones in good to excellent yields with complete retention of configuration at the α-amino- and α-alkoxy-substituted stereocenters.
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
authors.forename: Hao
authors.initials: H
authors.lastname: Li
authors.forename: Anyu
authors.initials: A
authors.lastname: He
authors.forename: John R
authors.initials: JR
authors.lastname: Falck
authors.forename: Lanny S
authors.initials: LS
authors.lastname: Liebeskind
mesh_terms: D000596:Amino Acids; D002264:Carboxylic Acids; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters; D006863:Hydrogen-Ion Concentration; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D004952:Esters; D007659:Ketones; D009947:Organotin Compounds; D010455:Peptides; D013438:Sulfhydryl Compounds; D013876:Thiophenes; C550746:2-thiophene carboxylic acid; D003300:Copper