Multicomponent reactions of phosphines, enynedioates and cinnamaldimines give γ-lactams with a 1,3,5-hexatriene moiety for facile 6π electrocyclization: Access to oxindoles, isatins and isoxazolinones

Jie Cheng Deng, Wu Yin Chen, Chaoyuan Zhu, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Multicomponent reactions of phosphines, enynedioates and cinnamaldimines generated 3-phosphorus ylide γ-lactams having a 1,3,5-hexatriene moiety with low activation energy barrier for 6π electrocyclization, through initial formation of 1,3-dipoles from the α(δ')-Michael addition of phosphines to enynedioates. The reactive 1,3-dipoles underwent addition to cinnamaldimines, lactamization, 6π electrocyclization and oxidation to give 3-phosphorus ylide oxindoles as platform molecules toward isatins and isoxazolinones. The key step, 6π electrocyclization, was further examined by a kinetic and a computational study.

Original languageEnglish
Pages (from-to)1453-1462
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number7
DOIs
StatePublished - 4 May 2015

Keywords

  • electrocyclic reactions
  • Michael addition
  • multicomponent reactions
  • phosphorus
  • transition states

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