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Enantioselective Iridium-Catalyzed Allylic Arylation
Authors:Damien Polet  Xavier Rathgeb  Caroline A. Falciola  Jean-Baptiste Langlois  Samir El Hajjaji  Alexandre Alexakis Prof.
Affiliation:Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-32-15
Abstract:We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.
Keywords:allylic substitution  asymmetric catalysis  chiral ligands  cross-coupling  iridium
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