Combinatorial Approach to Chiral Tris‐ligated Carbophilic Platinum Complexes: Application to Asymmetric Catalysis |
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Authors: | Dr Alexandre Pradal Prof Serafino Gladiali Dr Veronique Michelet Dr Patrick Y Toullec |
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Institution: | 1. Institut de Recherche de Chimie Paris, UMR 8247, Chimie ParisTech, ENSCP, 11, rue Pierre et Marie Curie, 75231 Paris CEDEX 05 (France), Fax: (+33)?144071062;2. Dipartimento di Chimica e Farmacia, Universita di Sassari, Via Vienna 2, 07100 Sassari (Italy) |
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Abstract: | A straightforward methodology for the synthesis of libraries of chiral tris‐ligated cationic platinum complexes and their in situ evaluation as asymmetric carbophilic catalysts in a model domino hydroarylation/cyclization reaction of a 1,6‐enyne was developed. A catalyst‐generation process based on a combination of a monodentate and a bidentate phosphorus ligand allowed the formation of 108 chiral complexes. One‐pot screening of the stereoinduction obtained with this library in a test domino addition/cyclization reaction validated this approach and stressed the key role played by the monodentate ligand partner in obtaining high enantioselectivities. In the case of two challenging substrate/nucleophile combinations, the combinatorial approach resulted in a significant gain in enantioselectivity. |
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Keywords: | asymmetric catalysis combinatorial chemistry cyclization platinum P ligands |
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