Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated. gamma.- …

H Nagashima, N Ozaki, M Ishii, K Seki…

Index: Nagashima, Hideo; Ozaki, Nobuyasu; Ishii, Masayuki; Seki, Koji; Washiyama, Masayoshi; Itoh, Kenji Journal of Organic Chemistry, 1993 , vol. 58, # 2 p. 464 - 470

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Citation Number: 128

Abstract

Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, BOC, Ts, or Ms group, are catalyzed by a 1: l mixture of CuCl and bipyridine to give the corresponding@, y-trichlorinated y-lactams in high yields. The reactions proceed at temperatures from-78 OC to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of ...