Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides

Hideo Nagashima, Hidetoshi Wakamatsu, Nobuyasu Ozaki, Tsutomu Ishii, Masakazu Watanabe, Tomonori Tajima, Kenji Itoh

研究成果: Contribution to journalArticle査読

108 被引用数 (Scopus)

抄録

A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated γ-lactams from allylic alcohols. No δ-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

本文言語英語
ページ(範囲)1682-1689
ページ数8
ジャーナルJournal of Organic Chemistry
57
6
DOI
出版ステータス出版済み - 3 1 1992
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 Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the [3.3]-Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides」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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