33861-29-9Relevant academic research and scientific papers
Tandem carbocupration/oxygenation of terminal alkynes
Zhang, Donghui,Ready, Joseph M.
, p. 5681 - 5683 (2005)
(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.
