Phosphine-Mediated Rauhut-Currier-Type/Acyl Transfer/ Wittig Strategy for Synthesis of Spirocyclopenta[c]chromene-Indolinones

Sandip Sambhaji Vagh, Bo Jhih Hou, Athukuri Edukondalu, Pin Ching Wang, Yi Ru Chen, Wenwei Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A phosphine-mediated reaction for the construction of spirocyclopenta[c]chromene-indolinones is reported via a Rauhut-Currier (RC)-type/acyl transfer/Wittig sequence. This methodology attributes the chemoselective phosphine addition to the alkynoate which generates the phosphorus zwitterion via RC-type reaction, and that further undergoes O-acylation to form the seven-membered betaine intermediate with acyl chloride in the presence of base. Extensive investigations reveal that the exceptional δ-acylation occurs through the C−O bond cleavage upon the seven-membered betaine, and the subsequent Wittig reaction preferentially result in the aforementioned spiro compounds. Furthermore, our protocol could also be applicable to different alkynoates to provide a series of spirocyclopenta[c]chromenones bearing privileged skeletons. (Figure presented.).

Original languageEnglish
Pages (from-to)5429-5435
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume363
Issue number24
DOIs
Publication statusPublished - 2021 Dec 21

Keywords

  • Rauhut-Currier reactions
  • Wittig reactions
  • phosphorus ylides
  • zwitterions
  • δ-acylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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