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

Research output: Contribution to journalArticle

107 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1682-1689
Number of pages8
JournalJournal of Organic Chemistry
Volume57
Issue number6
DOIs
Publication statusPublished - Mar 1 1992
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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