Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes

Bo Liang Zhao, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)

Abstract

A new diastereoselective and enantioselective cyclopropanation reaction has been developed by employing a Michael/alkylation cascade reaction between (E)-3-arylenechroman-4-one or (E)-2-arylideneindan-1-one derivatives and a bromonitroalkane with a chiral squaramide catalyst. This reaction constitutes a facile asymmetric synthesis for nitro-spirocyclopropanes that have three adjacent stereogenic centers, including one quaternary center, in moderate to good yields (up to 90%) with excellent enantio- [up to >99%ee (enantiomeric excess)] and diastereoselectivities [up to >99:1 dr (diastereomeric ratio)]. A cascade cyclopropanation reaction between (E)-3-arylenechroman-4-one or (E)-2-arylideneindan-1-one derivatives and a bromonitroalkane with a chiral squaramide catalyst has been developed. Nitro-spirocyclopropanes were obtained in moderate to good yields (up to 90%) with enantioselectivities up to >99%ee (enantiomeric excess) and diastereoselectivities up to >99:1 dr (diastereomeric ratio).

Original languageEnglish
Pages (from-to)5350-5359
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number24
DOIs
Publication statusPublished - 1 Aug 2015

Keywords

  • Alkylation
  • Asymmetric catalysis
  • Domino reactions
  • Michael addition
  • Organocatalysis
  • Spiro compounds

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Zhao, B. L., & Du, D. M. (2015). Chiral Squaramide-Catalyzed Michael/Alkylation Cascade Reaction for the Asymmetric Synthesis of Nitro-Spirocyclopropanes. European Journal of Organic Chemistry, 2015(24), 5350-5359. https://doi.org/10.1002/ejoc.201500533