論文

査読有り
2020年9月22日

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

Synthesis
  • Hiroshi Akutsu
  • ,
  • Kosuke Nakashima
  • ,
  • Yuta Kanetsuna
  • ,
  • Masahiro Kawada
  • ,
  • Shin-ichi Hirashima
  • ,
  • Tsuyoshi Miura

52
24
開始ページ
3874
終了ページ
3880
記述言語
掲載種別
研究論文(学術雑誌)
DOI
10.1055/s-0040-1707285
出版者・発行元
Georg Thieme Verlag KG

<title>Abstract</title>A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

リンク情報
DOI
https://doi.org/10.1055/s-0040-1707285
URL
http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707285.pdf
ID情報
  • DOI : 10.1055/s-0040-1707285
  • ISSN : 0039-7881
  • eISSN : 1437-210X

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