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

被引：28

作者：

Busqué, F

de March, P ^{[1
]}

Figueredo, M

Font, J

González, L

机构：

[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 07期

关键词：

lactones; Michael addition; sulfur; nucleophiles; furanones;

D O I：

10.1002/ejoc.200300693

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-alpha,beta-disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

引用

页码：1492 / 1499

页数：8

共 77 条

[1]

[Anonymous], [No title captured]

[2]

AYRES DC, 1990, LIGNANS

[3]

BEINER JM, 1972, CR ACAD SCI C CHIM, V274, P642

[4] 3-phenylselanylfuran-2(5H)-one:: a versatile building block in the synthesis of lignans.: A new approach towards 3,4-dibenzyl γ-butyrolactones [J].