Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines

Takumi Abe, Toshiki Yamashiro, Kaho Shimizu, Daisuke Sawada

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

This work reports the novel reactivity of hemiaminal as a precursor for indole editing at the multi-site. The HFIP-promoted indole editing of indoline hemiaminals affords 2-arylindoles through a ring-switch sequence. The key to success of this transformation is to use a cyclic hemiaminal as an α-amino aldehyde surrogate under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance. The utility of this transformation is presented through the one-pot protocol and the synthesis of isocryptolepine.

Original languageEnglish
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2022

Keywords

  • hemiaminals
  • HFIP
  • indoles
  • molecule editing
  • ring-switch

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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