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Combinatorial Approach to Chiral Tris‐ligated Carbophilic Platinum Complexes: Application to Asymmetric Catalysis
Author(s) -
Pradal Alexandre,
Gladiali Serafino,
Michelet Veronique,
Toullec Patrick Y.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304794
Subject(s) - denticity , chemistry , combinatorial chemistry , nucleophile , domino , ligand (biochemistry) , catalysis , enantioselective synthesis , chiral ligand , cationic polymerization , tris , platinum , stereochemistry , organic chemistry , metal , receptor , biochemistry
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.