Tandem carbocupration/oxygenation of terminal alkynes

Donghui Zhang, Joseph M. Ready

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

(Chemical Equation Presented) A direct and general synthesis of α-branched aldehydes and their enol derivatives is described. Carbocupration of terminal alkynes and subsequent oxygenation with lithium tert-butyl peroxide generates a metallo-enolate. Trapping with various electrophiles provides α-branched aldehydes or stereo-defined trisubstituted enol esters or silyl ethers. The tandem carbocupration/ oxygenation tolerates alkyl and silyl ethers, esters, and tertiary amines. The reaction is effective with organocopper complexes derived from primary, secondary, and tertiary Grignard reagents and from n-butyllithium.

Original languageEnglish (US)
Pages (from-to)5681-5683
Number of pages3
JournalOrganic Letters
Volume7
Issue number25
StatePublished - Dec 8 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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