Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions†
Dr. Diego A. Fort
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany) http://www.oc1.ch.tum.de/home_en/
Search for more papers by this authorDr. Thomas J. Woltering
Discovery Chemistry, PRCB, F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland)
Search for more papers by this authorDr. Matthias Nettekoven
Discovery Chemistry, PRCB, F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland)
Search for more papers by this authorDr. Henner Knust
Discovery Chemistry, PRCB, F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Thorsten Bach
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany) http://www.oc1.ch.tum.de/home_en/
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany) http://www.oc1.ch.tum.de/home_en/Search for more papers by this authorDr. Diego A. Fort
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany) http://www.oc1.ch.tum.de/home_en/
Search for more papers by this authorDr. Thomas J. Woltering
Discovery Chemistry, PRCB, F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland)
Search for more papers by this authorDr. Matthias Nettekoven
Discovery Chemistry, PRCB, F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland)
Search for more papers by this authorDr. Henner Knust
Discovery Chemistry, PRCB, F. Hoffmann-La Roche AG, Grenzacherstrasse 124, 4070 Basel (Switzerland)
Search for more papers by this authorCorresponding Author
Prof. Dr. Thorsten Bach
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany) http://www.oc1.ch.tum.de/home_en/
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching (Germany) http://www.oc1.ch.tum.de/home_en/Search for more papers by this authorD.A.F. wishes to acknowledge funding by the Roche Postdoc Fellowship (RPF) Program.
Graphical Abstract
Fabulous Fluorine: The synthesis of fluorinated products 1 and 2 by [2+2] photocycloaddition was readily feasible after optimization of the irradiation conditions. The electron-deficient trifluoroolefin unit reacted intramolecularly to products 1 (nine examples, d.r.>95:5). The reaction was also investigated after modification of position 2 of the side chain both with one or two fluoro substituents (e.g. to yield product 2).
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