Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo [g] quinolines

Xiaoyu Chen, James Theodore Merrett, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

21 Citations (Scopus)

Abstract

A synthetic method to prepare 1,2,3,5-tetrahydrobenzo[g]quinolines efficiently that relies on gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.

Original languageEnglish
Pages (from-to)1542-1545
Number of pages4
JournalOrganic Letters
Volume20
Issue number6
DOIs
Publication statusPublished - 16 Mar 2018

Keywords

  • Ynamide
  • Gold deposits
  • Formal [4+2]Cycloaddtion
  • quinolines
  • cascade catalysis

Cite this