115580-44-4Relevant academic research and scientific papers
PALLADIUM CATALYZED ALLYLIC C-ALKYLATION OF HIGHLY ACIDIC AND ENOLIC HETEROCYCLIC SUBSTRATES: TETRONIC ACID AND TRIACETIC ACID LACTONE
Moreno-Manas, Marcial,Prat, Maria,Ribas, Jordi,Virgili, Albert
, p. 581 - 584 (2007/10/02)
Tetronic acid (pKa 3.76) and triacetic acid lactone (pKa 4.94) have been alkylated at their active carbon atoms by means of thermodinamically controlled palladium catalyzed allylic alkylations.
Palladium-Catalyzed C-Alkylations of the Highly Acidic and Enolic Triacetic Acid Lactone. Mechanism and Stereochemistry
Moreno-Manas, Marcial,Ribas, Jordi,Virgili, Albert
, p. 5328 - 5335 (2007/10/02)
4-Hydroxy-6-methyl-2-pyrone (triacetic acid lactone) (1) is efficiently alkylated at C-3 with primary and secondary allylic substrates under thermodynamic control by using palladium(0) catalysts.Controlled hydrogenation of the resulting allylated derivatives affords pyrones with saturated chains at C-3.Allylic alkylations occur with retention of configuration at the allylic center, probably through a reversible kinetically favored O-alkylation.
