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

被引：29
作者：
Fort, Diego A. [1 ]
Woltering, Thomas J. [2 ]
Nettekoven, Matthias [2 ]
Knust, Henner [2 ]
Bach, Thorsten [1 ]
机构：
[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany
[2] F Hoffmann La Roche & Cie AG, Discovery Chem, PRCB, CH-4070 Basel, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 40期
关键词：
cycloaddition; diastereoselectivity; fluorine; photochemistry; strained molecules; MEDICINAL CHEMISTRY; VALENCE ISOMERS; REGIOSELECTIVITY; MECHANISM; ALKENES; CYCLOADDITION; DERIVATIVES; MOLECULES; OLEFINS; KETONES;
D O I：
10.1002/anie.201204080
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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页码：10169 / 10172
页数：4
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