Nucleophilic Conjugate 1,5-Addition of Gilman Reagents to (E)-Hex-2-en-4-ynedioates: An Access to β(γ')-Substituted Muconates

Hung Che Tai, Arjun S. Chavan, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

An unusual nucleophilic conjugate addition of organocuprates to enynedioates resulted in chemo- and regioselective formation of β( γ')-addition products, rather than α(δ')-addition products, in moderate to good yields. This addition pattern is different from that with organophosphanes or alkyl amines, and presents a short and efficient method for the preparation of various β(γ')-alkyl- or -aryl-substituted muconates compared with other synthetic approaches.

Original languageEnglish
Article numberss-2015-c0211-st
Pages (from-to)2223-2232
Number of pages10
JournalSynthesis (Germany)
Volume47
Issue number15
DOIs
StatePublished - 3 Aug 2015

Keywords

  • addition reactions
  • alkynes
  • cuprates
  • multicomponent reactions
  • regioselectivity

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