Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 13, Pages 3122-3131Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200204579
Keywords
acetylides; auto-catalysis; C-C coupling; conjugation; domino reactions
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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 multi-bond-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.
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