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- W1991750140 abstract "Treatment of γ-butyrolactone with bis[ethoxy(thiocarbonyl)] disulfide in the presence of 2.2 equiv of lithium diisopropylamide (LDA) produced lithium enolate of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate, which reacted with an aldehyde to afford exclusively (E)-α-alkylidene-γ-butyrolactone. Interestingly, when the reaction was quenched below −20 °C or when it was carried out in the presence of metal complex such as zinc chloride, copper(I) iodide, or tributyltin chloride, (Z)-α-alkylidene-γ-butyrolactone was obtained as the major product. The stereoselectivity of this reaction was sensitive to the reaction temperature and the metal cation employed." @default.
- W1991750140 created "2016-06-24" @default.
- W1991750140 creator A5087526551 @default.
- W1991750140 date "1987-05-01" @default.
- W1991750140 modified "2023-10-12" @default.
- W1991750140 title "Stereoselective Synthesis of (<i>E</i>)- or (<i>Z</i>)-α-Alkylidene-γ-butyrolactone from γ-Butyrolactone and Bis[ethoxy(thiocarbonyl)] Disulfide and Mechanistic Studies of the Effect of Metal Complexes on the Stereoselection" @default.
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- W1991750140 doi "https://doi.org/10.1246/bcsj.60.1853" @default.
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