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Synlett 1990; 1990(2): 67-73
DOI: 10.1055/s-1990-20991
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Carbonyl Group Regeneration with Substantive Enhancement of Structural Complexity

Leo A. Paquette*
  • *Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA
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Publication History

Publication Date:
08 March 2002 (online)

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The two-step process involving coupling of a β,γ-unsaturated ketone with a vinylic organometallic compound followed by oxy-Cope rearrangement (most often anionically accelerated) is shown to be capable of elaborating polycyclic ketones rapidly. The level of diastereoselection realizable in the first step, its high capacity for convergency, and the possibility of coupling the [3,3] sigmatropic isomerization with a subsequent chemical event combine to make the scheme a very powerful synthetic tool. 1. Introduction 2. Origins of the Oxy-Cope Rearrangement 3. Rapid Elaboration of Polycyclic Structures 4. Concise Assembly of Bridgehead Olefinic Ketones 5. Pairing of the Oxy-Cope Rearrangement with a Second Chemical Event 6. Diastereoselectivity Considerations 7. Future Prospects