Journal of Organic Chemistry p. 464 - 470 (1993)
Update date:2022-07-31
Topics:
Nagashima, Hideo
Ozaki, Nobuyasu
Ishii, Masayuki
Seki, Koji
Washiyama, Masayoshi
Itoh, Kenji
Cyclisations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding β,γ-trichlorinated γ-lactams in high yields.The reactions proceed at temperatures from -78 deg C to room temperature.Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the γ-lactams formed were dependent on the substituents on the nitrogen atom.The stereochemical outcome is compared with that of free-radical cyclization.
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