Catalytic enantioselective henry reactions of isatins: Application in the concise synthesis of (S)-(-)-spirobrassinin

Lu Liu, Shilei Zhang, Fei Xue, Guangshun Lou, Haoyi Zhang, Shichao Ma, Wenhu Duan, Wei Wang

Research output: Contribution to journalArticlepeer-review

99 Scopus citations

Abstract

When isatin a cat! A highly efficient, cupreine-catalyzed, enantioselective Henry reaction of readily available isatins and nitroalkanes has been developed (see scheme). The products are produced in excellent yields and good enantioselectivities under mild reaction conditions and without chromatography. The utility of the strategy has been demonstrated in the facile synthesis of (S)-(-)-spirobrassinin without the need for protecting groups.

Original languageEnglish (US)
Pages (from-to)7791-7795
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number28
DOIs
StatePublished - Jul 4 2011
Externally publishedYes

Keywords

  • Henry reaction
  • isatins
  • natural products
  • organocatalysis
  • oxindoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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