Volume 31, Issue 23
Heterocyclic Compounds
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ChemInform Abstract: Stereoselective Radical-Tandem Reaction of Aniline Derivatives with (5R)-5-Menthyloxy-2,5-dihydrofuran-2-one Initiated by Photochemical Induced Electron Transfer.

Samuel Bertrand

Samuel Bertrand

Lab. “React. Sel. Appl.”, CNRS, Fac. Sci., Univ. Reims-Champagne-Ardenne, F-51687 Reims, Fr.

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Norbert Hoffmann

Norbert Hoffmann

Lab. “React. Sel. Appl.”, CNRS, Fac. Sci., Univ. Reims-Champagne-Ardenne, F-51687 Reims, Fr.

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Jean-Pierre Pete

Jean-Pierre Pete

Lab. “React. Sel. Appl.”, CNRS, Fac. Sci., Univ. Reims-Champagne-Ardenne, F-51687 Reims, Fr.

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Veronique Bulach

Veronique Bulach

Lab. “React. Sel. Appl.”, CNRS, Fac. Sci., Univ. Reims-Champagne-Ardenne, F-51687 Reims, Fr.

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First published: 08 June 2010

Abstract

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ChemInform Abstract

The stereoselective addition of tertiary aromatic amines (II) and (V) to furanone (I) leads to the corresponding quinolines (III), (IV), (VI), and (VII) through a radical-tandem process. Under optimized reaction conditions, the facial diastereoselectivity is about 90%. In the reaction of (I) with (V) the configuration of the second chiral center is not efficiently controlled. Thus, the products (VI) and (VII) are obtained in similar yields.

chemical structure image

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