4.4 Article

Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between AuI and AuIII

Journal

TETRAHEDRON
Volume 65, Issue 9, Pages 1871-1879

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.112

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Funding

  1. CNRS
  2. French Ministry of Research

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omega-Acetylenic acids, Substituted or not at their acetylenic end, could be efficiently cyclized to gamma- or delta-alkylidene lactones in the presence of AuCl and K2CO3. In contrast AuCl3 led to lactone dimers, probably through cyclization and reductive dimerization. These Au-I and Au-III catalyzed cyclizations were totally regioselective and most often highly stereoselective. (C) 2008 Elsevier Ltd. All rights reserved.

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