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A Study of the Conjugate Addition of Thionucleophiles to 2(5 H )‐Furanones
Author(s) -
Busqué Felix,
de March Pedro,
Figueredo Marta,
Font Josep,
González Lluïsa
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300693
Subject(s) - chemistry , conjugate , thio , electrophile , addition reaction , adduct , substrate (aquarium) , hydrolysis , thiol , medicinal chemistry , organic chemistry , stereochemistry , catalysis , mathematical analysis , oceanography , mathematics , geology
Abstract Several new 4‐thio‐4,5‐dihydro‐2(3 H )‐furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5 H )‐furanones. When 5‐methyl‐2(5 H )‐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)