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

• Published in: Angewandte 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
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.10.2012; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Chemistry; Chemistry, Multidisciplinary; cycloaddition; diastereoselectivity; fluorine; Irradiation; photochemistry; Physical Sciences; Science & Technology; strained molecules; strained molecules; MECHANISM; diastereoselectivity; REGIOSELECTIVITY; MOLECULES; MEDICINAL CHEMISTRY; ALKENES; KETONES; cycloaddition; photochemistry; VALENCE ISOMERS; OLEFINS; DERIVATIVES; fluorine
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201204080

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).