C1-Symmetric Monosubstituted Chiral Diene Ligands in Asymmetric Rhodium-Catalyzed 1,4-Addition Reactions†
Thomas Gendrineau
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorOlivier Chuzel Dr.
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorHendrik Eijsberg
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorJean-Pierre Genet Prof.
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorSylvain Darses Dr.
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorThomas Gendrineau
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorOlivier Chuzel Dr.
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorHendrik Eijsberg
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorJean-Pierre Genet Prof.
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorSylvain Darses Dr.
Laboratoire de Synthèse Sélective Organique (UMR 7573), Ecole Nationale Supérieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris cedex 05 (France), Fax: (+33) 1-4407-1062
Search for more papers by this authorThis work was support by the Centre National de la Recherche Scientifique (CNRS). T. Gendrineau thanks the Ministère de l'Education et de la Recherche for a grant.
Graphical Abstract
One trumps two: Monosubstituted chiral bicyclo[2.2.2]octadiene ligands, derived from carvone, form complexes with rhodium to catalyze the asymmetric addition of boronic acid substrates to α,β-unsaturated ketones (see scheme). The 1,4-adducts are produced in good yield and high enantioselectivity.
Supporting Information
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