Tandem carbocupration/oxygenation of terminal alkynes

Donghui Zhang; Joseph M. Ready

doi:10.1021/ol052413g

Tandem carbocupration/oxygenation of terminal alkynes

Donghui Zhang, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	5681-5683
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	25
DOIs	https://doi.org/10.1021/ol052413g
State	Published - Dec 8 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol052413g

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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.",

author = "Donghui Zhang and Ready, {Joseph M.}",

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T1 - Tandem carbocupration/oxygenation of terminal alkynes

AU - Zhang, Donghui

AU - Ready, Joseph M.

PY - 2005/12/8

Y1 - 2005/12/8

N2 - (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.

AB - (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.

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Tandem carbocupration/oxygenation of terminal alkynes

Abstract

ASJC Scopus subject areas

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