
Journal of Organic Chemistry p. 5328 - 5335 (1988)
Update date:2022-08-04
Topics:
Moreno-Manas, Marcial
Ribas, Jordi
Virgili, Albert
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.
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