Base-Catalyzed domino double michael reactions of 1-hydroxy-1,4-dien-3-ones and 2-alkylidenemalononitriles: A diastereoselective route to polysubstituted 3-alkanoyl-4-hydroxycyclohex-3-enes

Yeong Jiunn Jang, Yu Shan Chen, Chia Jui Lee, Chi Han Chen, Wenwei Lin

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles catalyzed by triethylamine. This simple domino process affords a variety of highly functionalized 3-alkanoyl-4-hydroxycyclohex-3-enes, some of which are not easily accessible using other methodologies, in moderate to good yields and excellent diastereoselectivity (dr > 95:5). Thus, the generality of this process and feasibility of introducing bioactive moieties make this reaction highly valuable in synthetic and medicinal chemistry.

Original languageEnglish
Article numberss-2014-h0403-op
Pages (from-to)95-107
Number of pages13
JournalSynthesis (Germany)
Volume47
Issue number1
DOIs
Publication statusPublished - 2015 Jan

Keywords

  • Michael addition
  • curcumin
  • cyclohexanone
  • diastereoselectivity
  • domino reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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