An organocatalytic mannich/denitration reaction for the asymmetric synthesis of 3-ethylacetate-substitued 3-amino-2-oxindoles: Formal synthesis of AG-041R

Kun Zhao, Tao Shu, Jiaqi Jia, Gerhard Raabe, Dieter Enders*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

The highly enantioselective organocatalytic addition of ethyl nitroacetate to isatin-derived N-Boc ketimines (Boc = tert-butoxycarbonyl), followed by the removal of the nitro group, is described. The scalable reaction sequence leads to the title compounds as important intermediates of pyrroloindoline alkaloids and related drugs in excellent yields and enantioselectivities. The synthesis of the hexahydrofurano[2,3-b]indole skeleton, the spirocarbamate oxindole unit, and the formal synthesis of AG-041R have been carried out to demonstrate the synthetic utility of this protocol.

Original languageEnglish (US)
Pages (from-to)3933-3936
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number10
DOIs
StatePublished - Oct 7 2014

Bibliographical note

Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • Asymmetric synthesis
  • Ketimines
  • Mannich reaction
  • Organocatalysis
  • Oxindoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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