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ChemInform Abstract

Tricycle (I) and the bicyclic analogue (IV) undergo rhodium/chiral PPF ligand catalyzed ring-opening in the presence of a variety of secondary amines or phenols to give dihydronaphthalenoles and cyclohexenoles with high enantiomeric excesses and yields. The best results are obtained in most cases, if the chloride counterion of the rhodium complex is first removed by addition of AgOTf and the iodide is subsequently added in the form of Bu₄NI to generate a rhodium iodide/PPF complex in situ. The ring-opening of (I) with secondary amines such as pyrrolidine under rhodium/achiral ligand catalysis proceeds well either with Et₃N×HCl or Bu₄NI or Bu₄NI/CSA. The other tetrabutylammonium halides give only poor yields. For the reaction with primary amines, good yields are only obtained if Bu₄NI/CSA is added.