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Dr. Laina M. Geary, Dr. Sang Kook Woo, Joyce C. Leung and Prof. Michael J. Krische Diastereo- and Enantioselective Iridium-Catalyzed Carbonyl Propargylation from the Alcohol or Aldehyde Oxidation Level: 1,3-Enynes as Allenylmetal Equivalents Angewandte Chemie International Edition 51

Article first published online: 15 FEB 2012 | DOI: 10.1002/anie.201200239

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Axial to axial to point chirality transfer: Exposure of conjugated enynes to alcohols in the presence of an iridium catalyst modified by a segphos ligand results in the generation of aldehyde–allenyliridium pairs and formation of enantiomerically enriched products of carbonyl anti-(α-methyl)propargylation (see scheme). An identical set of products are obtained from aldehydes under related transfer hydrogenation conditions by employing formic acid as a reductant.

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