Penultimate group effects in free radical telomerizations of acrylamides

Article abstract of DOI:10.1016/0040-4020(96)00077-4

The telomerization of several acrylamides, most containing chiral auxiliary groups, was investigated. The first-formed stereogenic center in the n = 2 telomer (the penultimate center) has a significant effect on the configuration of the second (ultimate) center in the product. The penultimate chiral center of oxazolidine-derived acrylamides directs the configuration of the ultimate center such that the erythro n = 2 product is preferred. Sultam-substituted acrylamides preferentially lead, on the other hand, to threo products or give products with little stereoselectivity.