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Karl Anker Jørgensen

Organocatalytic [4+2] addition reactions via tetraenamine intermediate

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  • Julian Stiller, Aarhus Univ, Aarhus University, Ctr Catalysis, Dept Chem, Denmark
  • Pernille H. Poulsen, Aarhus Univ, Aarhus University, Ctr Catalysis, Dept Chem, Denmark
  • David Cruz, Denmark
  • Jorge Dourado, Aarhus Univ, Aarhus University, Ctr Catalysis, Dept Chem, Unknown
  • Rebecca Davis, Denmark
  • Karl Anker Jorgensen
The [4+2]-cycloaddition reaction of 3-olefinic oxindoles with a tetraenamine intermediate is presented. In the reaction, a novel class of highly functionalized spirocyclic cyclohexanes with four stereocenters is formed in high yield and excellent stereoselectivity. Mechanistic investigations and calculations point to a stepwise mechanism involving tetraenamine intermediates. Furthermore, several transformations are presented.
Original languageEnglish
JournalChemical Science
Volume5
Issue5
Pages (from-to)2052-2056
Number of pages5
ISSN2041-6520
DOIs
Publication statusPublished - 2014

    Research areas

  • DIELS-ALDER REACTIONS, ALPHA,BETA-UNSATURATED ALDEHYDES, ASYMMETRIC ORGANOCATALYSIS, DIENAMINE CATALYSIS, TRIENAMINES, 2,4-DIENALS, ACTIVATION, CONSTRUCTION, PRINCIPLE, OXINDOLES

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