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 in | Angewandte Chemie International Edition Vol. 51; no. 40; pp. 10169 - 10172 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
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Weinheim
WILEY-VCH Verlag
01.10.2012
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Edition | International ed. in English |
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ISSN | 1433-7851 1521-3773 |
DOI | 10.1002/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). |
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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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BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22962009$$D View this record in MEDLINE/PubMed |
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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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Notes | ark:/67375/WNG-31L4S1DT-5 ArticleID:ANIE201204080 D.A.F. wishes to acknowledge funding by the Roche Postdoc Fellowship (RPF) Program. istex:E1E89017FFB5009B066D06FFCDB5EB9ED7F0C798 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
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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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