CONJUGATE ADDITION-REACTIONS MEDIATED BY SAMARIUM(II) IODIDE

Samarium(II) iodide in conjunction with a catalytic low-valent transit ion metal species has been employed to promote the conjugate addition reaction of primary and secondary alkyl halides onto alpha,beta-unsatu rated esters and amides. The method has been determined to be quite ge neral and hence has been extended to the cyclization reactions of alky l halides onto alpha,beta-unsaturated lactones, lactams, and nitriles. The cyclization reactions described herein provide a very general app roach to the synthesis of functionalized carbocycles from simple acycl ic precursors with excellent diastereoselectivity and under very mild reaction conditions.