Highly stereoselective Friedel-Crafts type cyclization. Facile access to enantiopure 1,4-dihydro-4-phenyl isoquinolinones |
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Authors: | Nicolas PhilippeFranç ois Denivet,Jean-Luc VasseJana Sopkova-de Olivera Santos,Vincent Levacher,Georges Dupas |
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Affiliation: | a Laboratoire de Chimie Organique Fine et Hétérocyclique associé au CNRS, IRCOF-INSA, B.P. 08, F-76131 Mont Saint Aignan Cédex, France b UFR des Sciences Pharmaceutiques (CERMN). 5 rue Vaubénard F-14032 Caen, France |
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Abstract: | The present report describes a stereoselective synthesis of 1,4-dihydro-4-phenyl isoquinolinones 5 based on a stereoselective Friedel-Crafts type cyclization. Cyclization precursors 1 were prepared in two steps, from the readily available (S)-mandelic acid, in 60-80% overall yield. The stereoselective electrophilic cyclization was accomplished in 20-86% yield and with 20-97% ee. In the course of this work, the presence of the amide carbonyl was found to be particularly important to guarantee a stereospecific process during the electrophilic aromatic substitution. |
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Keywords: | Friedel-Crafts reaction cyclization isoquinolinone stereoselective |
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