4.4 Article

Synthesis of substituted tropones by sequential Rh-catalyzed [5+2] cycloaddition and elimination

Journal

TETRAHEDRON
Volume 71, Issue 35, Pages 5979-5984

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.04.039

Keywords

Tropone; Cycloaddition; Rhodium; 1,4-Enynes; Alkynes

Funding

  1. University of Wisconsin
  2. National Institute of Health [R01GM088285]
  3. Southern Medical University

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Highly substituted tropones are prepared from cycloheptatrienes derived from Rh-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and propargylic alcohols. The intermolecular [5+2] cycloaddition is highly regioselective for a variety of propargylic alcohols. Elimination of the cycloaddition products afforded various substituted tropones. (C) 2015 Elsevier Ltd. All rights reserved.

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