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Synlett 1996; 1996(4): 373-376
DOI: 10.1055/s-1996-5431
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Samarium(II) Iodide Promoted Ketone-Olefin Couplings Chelation-Controlled by (Alkoxycarbonyl)amino Groups

M. Kawatsura, F. Dekura, H. Shirahama, F. Matsuda*
  • *Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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The stereochemical course of the SmI2-induced intermolecular reductive couplings of the α-(alkoxycarbonyl)amino ketones with the α,β-unsaturated esters is completely stereocontrolled by chelation of the Sm(III) cations attached to the resulting ketyl radicals with the α-(alkoxycarbonyl)amino groups.

Samarium(II) Iodide - Ketone-Olefin Coupling - (Alkoxycarbonyl)amino Group