Extending Pummerer reaction chemistry. Asymmetric synthesis of spirocyclic oxindoles via chiral indole-2-sulfoxides

Ken S. Feldman, Andrew G. Karatjas

Research output: Contribution to journalArticlepeer-review

57 Scopus citations

Abstract

The conversion of (S8)-3-(ω-allylsilane and silyl enol ether)indole-2-sulfoxides to spirocyclic indolenines and then to oxindoles proceeds, in favorable cases, with moderate levels of chirality transfer from sulfur to C(3) of the indole core. A mechanistic model, which features either an Sn2′-like additive Pummerer sequence or a tight ion pair generated by an Sn1-like vinylogous Pummerer transform, is proposed to rationalize the sense of asymmetric induction.

Original languageEnglish (US)
Pages (from-to)4137-4140
Number of pages4
JournalOrganic Letters
Volume8
Issue number18
DOIs
StatePublished - Aug 31 2006

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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