Efficient domino process based on the catalytic generation of non-metalated, conjugated acetylides in the presence of aldehydes or activated ketones.
The extremely mild and highly efficient catalytic generation of non-metalated, conjugated acetylides is reported. These acetylides are used to generate enol-protected functionalized propargylic alcohols 1, 1,3-dioxolane compounds 2, or 3,4,5-trisubstituted 4,5-dihydrofurans 4 through serial multibond-forming processes. The method calls for a nucleophile (a tertiary amine or phosphine) as a chemical activator, a conjugated terminal acetylene as the acetylide source, and an aldehyde or activated ketone as the electrophilic partner. The chemical outcome of this process depends on the nature of the nucleophile, the temperature, stoichiometry and solvent, and it can be tailored selectively by the appropriate choice of the experimental conditions.
Tejedor
David
D
Instituto de Productos Naturales y Agrobiología Consejo Superior de Investigaciones Científicas Avda. Astrofísico Francisco Sánchez 3 38206 La Laguna, Tenerife, Spain.
García-Tellado
Fernando
F
Marrero-Tellado
José Juan
JJ
de Armas
Pedro
P
D000447:Aldehydes / Q000737:chemistry* / Q000378:metabolism*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry* / Q000378:metabolism*
D000447:Aldehydes; D007659:Ketones