title: Decarbonylative radical coupling of α-aminoacyl tellurides: single-step preparation of γ-amino and α,β-diamino acids and rapid synthesis of gabapentin and manzacidin A.
abstract: A new radical-based coupling method has been developed for the single-step generation of various γ-amino acids and α,β-diamino acids from α-aminoacyl tellurides. Upon activation by Et3 B and O2 at ambient temperature, α-aminoacyl tellurides were readily converted into α-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (-)-manzacidin A.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
authors.forename: Masanori
authors.initials: M
authors.lastname: Nagatomo
authors.forename: Hayato
authors.initials: H
authors.lastname: Nishiyama
authors.forename: Haruka
authors.initials: H
authors.lastname: Fujino
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D003509:Cyclohexanecarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003653:Decarboxylation; D004987:Ethers / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D000077206:Gabapentin; D006038:Glyoxylates / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013691:Tellurium / Q000737:chemistry*; D005680:gamma-Aminobutyric Acid / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D000596:Amino Acids; D003509:Cyclohexanecarboxylic Acids; D004987:Ethers; D005609:Free Radicals; D006038:Glyoxylates; D011743:Pyrimidines; D011758:Pyrroles; C482355:glyoxylic oxime ether; C470325:manzacidin A; D005680:gamma-Aminobutyric Acid; D000077206:Gabapentin; D013691:Tellurium
keywords: amino acids; natural products; radical reactions; tellurium; total synthesis