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Complex Carbocyclic Skeletons from Aryl Ketones through a Three‐Photon Cascade Reaction
Author(s) -
Næsborg Line,
Jandl Christian,
Zech Andreas,
Bach Thorsten
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915731
Subject(s) - conrotatory and disrotatory , cyclopropane , chemistry , ring (chemistry) , cycloaddition , aryl , carbon skeleton , yield (engineering) , isomerization , claisen rearrangement , cascade , stereochemistry , photochemistry , organic chemistry , catalysis , materials science , alkyl , metallurgy , chromatography
Starting from readily available 7‐substituted 1‐indanones, products with a tetracyclo[5.3.1.0 1,7 0 4,11 ]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[5.3.1.0 4,11 ]undec‐2‐enes and of tricyclo[6.2.1.0 1,5 ]undecanes.