Samarium(II) iodide-mediated intramolecular conjugate additions of alpha,beta-unsaturated lactones.
Samarium(II) iodide, in the presence of catalytic amounts of nickel(II) iodide, has been used to promote intramolecular conjugate additions of alkyl halides onto alpha,beta-unsaturated lactones. This process has been shown to be applicable to a number of alpha,beta-unsaturated lactones, including tetrasubstituted olefins, and has been demonstrated to be quite general for the formation of saturated bicyclic and tricyclic lactones. The method presented herein provides a mild, efficient process to form structurally complex lactones from simple precursors.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA. gmolandr@sas.upenn.edu
St  Jean
David J
DJ
D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D012493:Samarium / Q000737:chemistry*
D006846:Hydrocarbons, Halogenated; D007454:Iodides; D007783:Lactones; D012493:Samarium; C409809:samarium diiodide