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Synlett 1995; 1995(7): 729-732
DOI: 10.1055/s-1995-5066
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Samarium(II) Iodide Mediated Intermolecular Ketone-Olefin Couplings Chelation-Controlled by β-Hydroxyl Groups

M. Kawatsura, K. Hosaka, F. Matsuda* , H. Shirahama
  • *Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060, Japan
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Publication Date:
31 December 2000 (online)

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The stereochemical course of the SmI2-induced intermolecular reductive couplings of the β-hydroxy aldehyde 1 and the β-hydroxy ketone 4 is completely stereocontrolled by chelation of the Sm(III) cations attached to the resulting ketyl radicals with the β-hydroxyl groups providing the anti-1,3-diols 2 and 5, respectively.

Samarium(II) Iodide - Ketone-Olefin Coupling - β-Hydroxyl Group