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.

引用

页码：10169 / 10172

页数：4

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