Tetrahedron

Penultimate group effects in free radical telomerizations of acrylamides

NA Porter, RL Carter, CL Mero, MG Roepel, DP Curran

Index: Porter, Ned A.; Carter, Randall L.; Mero, Christopher L.; Roepel, Michael G.; Curran, Dennis P. Tetrahedron, 1996 , vol. 52, # 12 p. 4181 - 4198

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Citation Number: 21

Abstract

The telomerizaton 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 ...

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