Asymmetric organocatalyzed Michael addition of nitromethane to a 2-oxoindoline-3-ylidene acetaldehyde and the three one-pot sequential synthesis of (-)-horsfiline and (-)-coerulescine

Takasuke Mukaiyama, Kento Ogata, Itaru Sato, Yujiro Hayashi

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

(-)-Horsfiline and (-)-coerulescine were synthesized through three one-pot operations in 33 and 46% overall yield, respectively. Key to the success was the efficient use of a diarylprolinol silyl ether to catalyze the asymmetric Michael addition of nitromethane to a 2-oxoindoline-3-ylidene acetaldehyde. This allowed the all-carbon quaternary, spirocyclic carbon stereocenter to be constructed in good yield with excellent enantioselectivity.

Original languageEnglish
Pages (from-to)13583-13588
Number of pages6
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume20
Issue number42
DOIs
Publication statusPublished - 2014 Oct 13

Keywords

  • Michael addition
  • alkaloids
  • asymmetric synthesis
  • one-pot reactions
  • organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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