Conjugate Addition Reactions Mediated by Samarium(II) Iodide.
Samarium(II) iodide in conjunction with a catalytic low-valent transition metal species has been employed to promote the conjugate addition reaction of primary and secondary alkyl halides onto alpha,beta-unsaturated esters and amides. The method has been determined to be quite general and hence has been extended to the cyclization reactions of alkyl halides onto alpha,beta-unsaturated lactones, lactams, and nitriles. The cyclization reactions described herein provide a very general approach to the synthesis of functionalized carbocycles from simple acyclic precursors with excellent diastereoselectivity and under very mild reaction conditions.
Molander
Gary A.
GA
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215.
Harris
Christina R.
CR