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

研究成果: 雜誌貢獻文章同行評審

6 引文 斯高帕斯(Scopus)

摘要

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.

原文英語
文章編號ss-2014-h0403-op
頁(從 - 到)95-107
頁數13
期刊Synthesis (Germany)
47
發行號1
DOIs
出版狀態已發佈 - 2015 一月

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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