Journal of Organic Chemistry 2002-05-31

Samarium(II) iodide-mediated intramolecular conjugate additions of alpha,beta-unsaturated lactones.

Gary A Molander, David J St Jean

Index: J. Org. Chem. 67(11) , 3861-5, (2002)

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Abstract

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.