A tandem carbanion addition/carbon-carbon bond cleavage yields alkynyl ketones.
Carbanion addition to vinylogous acid triflates triggers carbon-carbon bond cleavage to form alkynyl ketones under mild conditions. Mechanistic factors affecting the cleavage event and its relationship to complementary fragmentations are discussed. A range of tethered keto-alkynes are obtained by a unified approach.
Kamijo
Shin
S
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, USA.
Dudley
Gregory B
GB