Tandem carbocupration/oxygenation of terminal alkynes

Donghui Zhang, Joseph M. Ready

Research output: Contribution to journalArticle

32 Citations (Scopus)

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
DOIs
StatePublished - Dec 8 2005

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Oxygenation
Alkynes
Ethers
oxygenation
alkynes
aldehydes
Aldehydes
esters
ethers
Esters
peroxides
Lithium
Amines
reagents
amines
lithium
trapping
Derivatives
synthesis
n-butyllithium

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Tandem carbocupration/oxygenation of terminal alkynes. / Zhang, Donghui; Ready, Joseph M.

In: Organic Letters, Vol. 7, No. 25, 08.12.2005, p. 5681-5683.

Research output: Contribution to journalArticle

Zhang, Donghui ; Ready, Joseph M. / Tandem carbocupration/oxygenation of terminal alkynes. In: Organic Letters. 2005 ; Vol. 7, No. 25. pp. 5681-5683.
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