Palladium-Catalyzed C-Alkylations of the Highly Acidic and Enolictriacetic Acid Lactone. Mechanism and Stereochemistry

Marcial Moreno-Mañas, Jordi Ribas, Albert Virgili

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58 Citations (Scopus)

Abstract

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. © 1988, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)5328-5335
JournalJournal of Organic Chemistry
Volume53
Issue number22
DOIs
Publication statusPublished - 1 Oct 1988

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