Rhodium(I)-Catalyzed Domino Asymmetric Ring Opening/Enantioselective Isomerization of Oxabicyclic Alkenes with Water


  • This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), the Merck Frosst Centre for Therapeutic Research, and the University of Toronto. We gratefully thank Dr. Alan Lough (Chemistry Department, University of Toronto) for single-crystal X-ray structure analysis, Dr. Bernard Leroy for the initial studies using azabicycles, and Solvias AG for the generous gift of chiral ligands.


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Water-induced asymmetric ring opening: Enantio-enriched 2-hydroxy-1-tetralones are formed from oxabicyclic alkenes through a novel RhI-catalyzed domino reaction. The proposed mechanism involves water-induced asymmetric ring opening to generate chiral trans-1,2-diol intermediates and subsequent enantioselective isomerization (see scheme).