Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions

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...

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Published inAngewandte Chemie International Edition Vol. 51; no. 40; pp. 10169 - 10172
Main Authors Fort, Diego A., Woltering, Thomas J., Nettekoven, Matthias, Knust, Henner, Bach, Thorsten
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.10.2012
WILEY‐VCH Verlag
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ISSN1433-7851
1521-3773
DOI10.1002/anie.201204080

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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).
AbstractList 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).
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 position2 of the side chain both with one or two fluoro substituents (e.g. to yield product 2).
Author Woltering, Thomas J.
Fort, Diego A.
Nettekoven, Matthias
Knust, Henner
Bach, Thorsten
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Keywords strained molecules
MECHANISM
diastereoselectivity
REGIOSELECTIVITY
MOLECULES
MEDICINAL CHEMISTRY
ALKENES
KETONES
cycloaddition
photochemistry
VALENCE ISOMERS
OLEFINS
DERIVATIVES
fluorine
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Snippet Fabulous Fluorine: The synthesis of fluorinated products 1 and 2 by [2+2] photocycloaddition was readily feasible after optimization of the irradiation...
Fabulous Fluorine: The synthesis of fluorinated products 1 and 2 by [2+2]photocycloaddition was readily feasible after optimization of the irradiation...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
cycloaddition
diastereoselectivity
fluorine
Irradiation
photochemistry
Physical Sciences
Science & Technology
strained molecules
Title Synthesis of Fluorinated Tricyclic Scaffolds by Intramolecular [2+2] Photocycloaddition Reactions
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