Synthesis of Highly Functionalized Cyclohexenone Rings: Rhodium-Catalyzed 1,3-Acyloxy Migration and Subsequent [5+1] Cycloaddition


  • We thank the NIH (R01GM088285) and the University of Wisconsin for funding.


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Lead Rh-ole: Highly substituted cyclohexenones were prepared from cyclopropyl-substituted propargyl esters by using a [{Rh(CO)2Cl}2] catalyst. This metal catalyst promoted the 1,3-acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the presence of CO with high regioselectivity.