Complex Carbocyclic Skeletons from Aryl Ketones through a Three-Photon Cascade Reaction

Line Næsborg, Christian Jandl, Andreas Zech, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Starting from readily available 7-substituted 1-indanones, products with a tetracyclo[5.3.1.01,704,11]undec-2-ene skeleton were obtained upon irradiation at λ=350 nm (eight examples, 49–67 % yield). The assembly of the structurally complex carbon framework proceeds in a three-photon process comprising an ortho photocycloaddition, a disrotatory [4π] photocyclization, and a di-π-methane rearrangement. The flat aromatic core of the starting material is converted into a functionalized polycyclic hydrocarbon with exit vectors in three dimensions. Ring opening reactions at the central cyclopropane ring were explored, which enable the preparation of tricyclo[5.3.1.04,11]undec-2-enes and of tricyclo[6.2.1.01,5]undecanes.

Original languageEnglish
Pages (from-to)5656-5659
Number of pages4
JournalAngewandte Chemie International Edition in English
Volume59
Issue number14
DOIs
StatePublished - 27 Mar 2020

Keywords

  • carbocycles
  • domino reactions
  • pericyclic reactions
  • photochemistry
  • rearrangement

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