1418030-75-7Relevant academic research and scientific papers
Photocycloaddition of 3-alkenyloxy-2-cycloalkenones: Enantioselective lewis acid catalysis and ring expansion
Brimioulle, Richard,Bach, Thorsten
supporting information, p. 12921 - 12924 (2016/02/18)
By application of substoichiometric amounts (50 mol %) of a chiral Lewis acid, the intramolecular [2+2] photocycloaddition of the title compounds was achieved with high enantioselectivity (up to 94 % ee). Upon cleavage of the cyclobutane ring the resulting tricyclic products underwent ring-expansion reactions under acidic conditions and formed anellated seven- or eight-membered-ring systems without racemization. The ring expansion could be combined with a diastereoselective reduction (triethylsilane) or allylation (allyltrimethylsilane) upon BF3 catalysis (48-87 % yield). Ring-a-ring o'roses: An enantioselective, Lewis acid catalyzed [2+2] photocycloaddition (9 examples, 69-94 % yield, up to 94 % ee) leads to tricyclic products, in which the marked bond of the cyclobutane ring can be cleaved to form medium-sized rings as shown in the example above.
Synthesis of fluorinated tricyclic scaffolds by intramolecular [2+2] photocycloaddition reactions
Fort, Diego A.,Woltering, Thomas J.,Nettekoven, Matthias,Knust, Henner,Bach, Thorsten
supporting information, p. 10169 - 10172 (2012/11/07)
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 ex
