Transition Metal-Catalyzed Radical Cyclizations: A Low-Temperature Process for the Cyclization of N-Protected N-Allyltrichloroacetamides to Trichlorinated γ-Lactams and Application to the Stereoselective Preparation of β,γ-Disubstituted γ-Lactams

Hideo Nagashima, Nobuyasu Ozaki, Masayuki Ishii, Koji Seki, Masayoshi Washiyama, Kenji Itoh

研究成果: Contribution to journalArticle査読

133 被引用数 (Scopus)

抄録

Cyclizations 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 °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.

本文言語英語
ページ(範囲)464-470
ページ数7
ジャーナルJournal of Organic Chemistry
58
2
DOI
出版ステータス出版済み - 1 1 1993
外部発表はい

All Science Journal Classification (ASJC) codes

  • 有機化学

フィンガープリント

「Transition Metal-Catalyzed Radical Cyclizations: A Low-Temperature Process for the Cyclization of N-Protected N-Allyltrichloroacetamides to Trichlorinated γ-Lactams and Application to the Stereoselective Preparation of β,γ-Disubstituted γ-Lactams」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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