An Unprecedented Organocascade Synthesis of Functionalized Bicyclic Nitrones from 2-Aminomalonate Derived Nucleophiles and 1-Nitro-1,3-Enynes via Allenes Formation and Subsequent Rearrangement

Wan Yun Huang, Ramani Gurubrahamam, Kwunmin Chen

研究成果: 雜誌貢獻文章

1 引文 斯高帕斯(Scopus)

摘要

An efficient organocatalytic cascade reaction for synthesising functionalized bicyclic nitrones is reported. The reaction of dielectrophilic ethyl 2-(nitromethylene)-4-arylbut-3-ynoate and (E)-diethyl 2-((2-hydroxybenzylidene)-amino)malonates to give a unique nitrone scaffold in the presence of a catalytic amount of DABCO is described. The working mechanism was proposed to proceed with allene formation followed by intramolecular cyclization and the rearrangement of an oxygen atom in the nitro group. A broad range of substrates was accessed in this facile chemical transformation, in which the bicyclic nitrones were isolated in moderate to good yields (19% to 79%) with excellent diastereoselectivity (>20:1 dr). (Figure presented.).

原文英語
頁(從 - 到)170-175
頁數6
期刊Advanced Synthesis and Catalysis
361
發行號1
DOIs
出版狀態已發佈 - 2019 一月 11

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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