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

Marcial Moreno-Mañas; Jordi Ribas; Albert Virgili

doi:10.1021/jo00257a023

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

Marcial Moreno-Mañas, Jordi Ribas, Albert Virgili

Department of Chemistry

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59 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 language	English
Pages (from-to)	5328-5335
Journal	Journal of Organic Chemistry
Volume	53
Issue number	22
DOIs	https://doi.org/10.1021/jo00257a023
Publication status	Published - 1 Oct 1988

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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. {\textcopyright} 1988, American Chemical Society. All rights reserved.",

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T1 - Palladium-Catalyzed C-Alkylations of the Highly Acidic and Enolictriacetic Acid Lactone. Mechanism and Stereochemistry

AU - Moreno-Mañas, Marcial

AU - Ribas, Jordi

AU - Virgili, Albert

PY - 1988/10/1

Y1 - 1988/10/1

N2 - 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.

AB - 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.

U2 - 10.1021/jo00257a023

DO - 10.1021/jo00257a023

M3 - Article

SN - 0022-3263

VL - 53

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

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

Abstract

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