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Chiral squaramide-catalyzed highly enantioselective michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes

  • Wen Yang
  • , Da Ming Du*
  • *Corresponding author for this work
  • Beijing Institute of Technology

Research output: Contribution to journalArticlepeer-review

Abstract

A chiral squaramide-organocatalyzed, highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes has been developed. This reaction afforded the chiral naphthoquinones in excellent yields (up to 99%) and excellent enantioselectivity (up to 98% ee) under very low catalyst loading (0.25 mol%). This organocatalytic asymmetric Michael addition provides an efficient alternative route toward the synthesis of chiral functionalized naphthoquinones.

Original languageEnglish
Pages (from-to)1241-1246
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number8
DOIs
Publication statusPublished - May 2011

Keywords

  • Michael addition
  • asymmetric catalysis
  • naphthoquinones
  • nitroalkenes
  • organocatalysis
  • squaramides

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