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Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions
Author(s) -
Fort Diego A.,
Woltering Thomas J.,
Nettekoven Matthias,
Knust Henner,
Bach Thorsten
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204080
Subject(s) - intramolecular force , yield (engineering) , chemistry , tricyclic , fluorine , product (mathematics) , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , materials science , geometry , metallurgy
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 ).