Gold-Catalyzed Bicyclic and [3+2]-Annulations of Internal Propargyl Alcohols with Nitrones and Imines To Yield to Two Distinct Heterocycles

Sayaji Arjun More, Tzu Hsuan Chao, Mu Jeng Cheng, Rai Shung Liu

研究成果: Article同行評審

1 引文 斯高帕斯(Scopus)

摘要

A gold-catalyzed synthesis of 1,3-dihydrooxazolo[3,4-a]indoles from 1-oxo-3-yn-4-ols and nitrones is described; this new bicyclic annulation presents the first examples that internal alkynes can react with nitrones to undergo an oxoarylation route. DFT calculations indicate a [3,3]-sigmatropic shift of initial alkenylgold intermediates to elude the intermediacy of gold carbenes. We also developed new [3+2]-annulations of the same 1-oxo-3-yn-4-ols with imines, yielding oxazolidin-4-ylidene derivatives efficiently. The tethered alcohols of these 1-oxo-3-ynes allow trapping of their metastable 2-azadienium intermediates to enable a novel annulation. Our mechanistic analysis indicates that the two products, despite their structural relevance, are produced from two independent systems. (Figure presented.).

原文English
頁(從 - 到)525-531
頁數7
期刊Advanced Synthesis and Catalysis
363
發行號2
DOIs
出版狀態Published - 2021 一月 19

All Science Journal Classification (ASJC) codes

  • 催化
  • 有機化學

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