Dielectrophilic Allenic Ketone-Enabled [4 + 2] Annulation with 3,3'-Bisoxindoles: Enantioselective Creation of Two Contiguous Quaternary Stereogenic Centers

Xiaodong Tang, Chuan Xiang Alvin Tan, Wai Lun Chan, Fuhao Zhang, Wenrui Zheng, Yixin Lu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

3 Citations (Scopus)

Abstract

We introduced a type of allenic ketone as a dielectrophilic C4 synthon in phosphine-mediated reactions. The high electrophilicity of the advanced intermediates created upon phosphine activation empowered the utilization of 3,3′-bis-oxindoles as a two-carbon reaction partner in a highly enantioselective [4 + 2] annulation, allowing for facile creation of spirocyclic bisindoline structures containing two contiguous quaternary stereogenic centers. Synthetic manipulations of the [4 + 2] annulation product led to concise total synthesis of (-)-folicanthine.

Original languageEnglish
Pages (from-to)1361-1367
Number of pages7
JournalACS Catalysis
Volume11
Issue number3
DOIs
Publication statusPublished - 5 Feb 2021
Externally publishedYes

Keywords

  • allenic ketone
  • bifunctional phosphine
  • dielectrophilic
  • dinucleophilic
  • quaternary stereogenic centers
  • [4 + 2] annulation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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