Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes

Robert B. Lettan, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

73 Scopus citations


(Chemical Equation Presented) The Lewis base-catalyzed additions of alkynyl nucleophiles to aldehydes, ketones, and imines is described. Mechanistic studies strongly indicate that the use of new triethoxysilylalkynes facilitates access of a reactive hypervalent silicate intermediate. This activated carbon nucleophile subsequently undergoes rapid addition to carbonyl compounds and imines, thus affording the secondary and tertiary propargyl systems in moderate to high yield.

Original languageEnglish (US)
Pages (from-to)3227-3230
Number of pages4
JournalOrganic Letters
Issue number15
StatePublished - Jul 21 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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