Synthetic uses of ynolates

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57 Citations (Scopus)

Abstract

The synthetic uses of ynolates, including silyl ynol ethers, that has the ability to synthesize another reactive species are investigated. An ynolate, a nucleophile, reacts with an electrophile to give a ketene, an electrophile, which reacts with a nucleophile to afford an enolate, a nucleophile. Metalation of the precursors of ketenes, followed by transformation into the metalated ketenes, would be a better route to ynolates. An efficient method for the synthesis of ynolates has been developed which are easily converted into ketenes by elimination of alkoxides. Ynolate anions initiate a negative-positive switching cascade process, torquoselective olefination, and heterocyclization, and silyl ynol ethers act as functional electron-rich triple bond and ketenium precursors.

Original languageEnglish
Pages (from-to)10-36
Number of pages27
JournalTetrahedron
Volume63
Issue number1
DOIs
Publication statusPublished - Jan 1 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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