Gold-Catalyzed Intramolecular Allylic Amination of 2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (±)-Angustureine

Dataset UNKNOWN
Kothandaraman, Prasath; Foo, Shi Jia; Wai Hong Chan, Philip;
(2009)
  • Publisher: Figshare
  • Related identifiers: doi: 10.1021/jo900917q.s004, doi: 10.1021/jo900917q.s003, doi: 10.1021/jo900917q.s002, doi: 10.1021/jo900917q.s006, doi: 10.1021/jo900917q.s005
  • Subject: Molecular Biology | allylic cation moiety | substrate combinations | Biotechnology | room temperature | Developmental Biology | Sociology | Microbiology | dihydroquinoline | Concise Synthesis | Computational Biology | Marine Biology | AuCl | Ecology | sulfonamide unit | causes intramolecular nucleophilic addition | Biochemistry | Pharmacology | silver catalyst combination | tosylaminophenylprop | alcohol substrate | Biophysics
    • FOR: 110309 Infectious Diseases | 39999 Chemical Sciences not elsewhere classified

An efficient synthetic route to 1,2-dihydroquinolines that relies on AuCl<sub>3</sub>/AgSbF<sub>6</sub>-catalyzed intramolecular allylic amination of 2-tosylaminophenylprop-1-en-3-ols is described herein. Uniquely, the reactions were found to only proceed rapidly at roo... View more
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