How Do Analogous α-Chloroenamides and α-Iodoenamides Give Different Product Distributions in 5-Endo Radical Cyclizations?

DP Curran, DB Guthrie, SJ Geib

Index: Curran, Dennis P.; Guthrie, David B.; Geib, Steven J. Journal of the American Chemical Society, 2008 , vol. 130, # 26 p. 8437 - 8445

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Citation Number: 32

Abstract

5-Endo cyclizations of N-alkenyl carbamoylmethyl radicals provide γ-lactam radicals, which in turn evolve to reduced or non-reduced (alkene) products depending on reagents and reaction conditions. Several groups have made surprising observations that chlorides are better radical precursors than iodides in such cyclizations. Here is described a detailed study of tin and silicon hydride-mediated radical cyclizations of N-benzyl-2-halo-N- ...