Homoallylic alcohols from samarium diiodide-mediated coupling of allylic sulfones with carbonyl compounds
作者:Jonathan Clayden、Marc Julia
DOI:10.1039/c39940002261
日期:——
Reduction of allylic sulfones with samarium diiodide gives allylsamarium species which react in situ with carbonyl compounds, yielding homoallylic alcohols.
Preparation and reactions of samarium diiodide in nitriles
作者:Béatrice Hamann、Jean-Louis Namy、Henri B. Kagan
DOI:10.1016/0040-4020(96)00861-7
日期:1996.11
Samarium diiodide can be prepared from samarium metal in various nitriles. Because of its chemical inertness pivalonitrile is the most suitable solvent. Organic reactions mediated by SmI2 are slower than in THF, but selectivities are often improved. Reactions are greatly accelerated by addition of catalytic amounts of some transition metal salts.
Allylic phosphates allylate ketones and aldehydes in the presence of samarium(II) iodide. The coupling proceeds with the preservation of the olefin geometry, however, regio- and stereoselectivity are not high.
Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents