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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

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Volume 78, Issue 2


Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation

Barbara A. Messerle
  • Corresponding author
  • School of Chemistry, University of New South Wales, Kensington, NSW 2052, Australia
  • Other articles by this author:
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/ Khuong Q. Vuong
  • Corresponding author
  • School of Chemistry, University of New South Wales, Kensington, NSW 2052, Australia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200678020385

A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The iridium complex [Ir(PyP)(CO)2]BPh4 where PyP = 1-[(2-diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereoselective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-ethynylhexane-1,6-diol. The cycloadditions occur in all but one case with quantitative conversion in under 24 h at 120 °C.

Keywords: alkyne diols; catalysis; hydroalkoxylation; spiroketals; transition metals


IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 13th, Geneva, Switzerland, 2005-07-17–2005-07-21

About the article

Published Online: 2009-01-01

Published in Print: 2006-01-01

Citation Information: Pure and Applied Chemistry, Volume 78, Issue 2, Pages 385–390, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200678020385.

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