A study of the conjugate addition of thionucleophiles to 2(5H)-furanones

Felix Busqué; Pedro De March; Marta Figueredo; Josep Font; Lluïsa González

doi:10.1002/ejoc.200300693

A study of the conjugate addition of thionucleophiles to 2(5H)-furanones

Felix Busqué, Pedro De March, Marta Figueredo, Josep Font, Lluïsa González

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

28 Citations (Scopus)

Abstract

Several new 4-thio-4,5-dihydro-2(3H)-furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)-furanones. When 5-methyl-2(5H)-furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis-α,β-disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Original language	English
Pages (from-to)	1492-1499
Journal	European Journal of Organic Chemistry
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.200300693
Publication status	Published - 26 Mar 2004

Keywords

Furanones
Lactones
Michael addition
Nucleophiles
Sulfur

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abstract = "Several new 4-thio-4,5-dihydro-2(3H)-furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)-furanones. When 5-methyl-2(5H)-furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis-α,β-disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. {\textcopyright} Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.",

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T1 - A study of the conjugate addition of thionucleophiles to 2(5H)-furanones

AU - Busqué, Felix

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - González, Lluïsa

PY - 2004/3/26

Y1 - 2004/3/26

N2 - Several new 4-thio-4,5-dihydro-2(3H)-furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)-furanones. When 5-methyl-2(5H)-furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis-α,β-disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

AB - Several new 4-thio-4,5-dihydro-2(3H)-furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)-furanones. When 5-methyl-2(5H)-furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis-α,β-disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

KW - Furanones

KW - Lactones

KW - Michael addition

KW - Nucleophiles

KW - Sulfur

U2 - 10.1002/ejoc.200300693

DO - 10.1002/ejoc.200300693

M3 - Article

SP - 1492

EP - 1499

IS - 7

ER -

A study of the conjugate addition of thionucleophiles to 2(5H)-furanones

Abstract

Keywords

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