Stereoselective synthesis of (E)-or (Z)-.ALPHA.-alkylidene-.GAMMA.-butyrolactone from .GAMMA.-butyrolactone and bis[ethoxy(thiocarbonyl)] disulfide and mechanistic studies of the effect of metal complexes on the stereoselection.

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概要

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• Treatment of γ-butyrolactone with bis[ethoxy(thiocarbonyl)] disulfide in the presence of 2.2 equiv of lithium diisopropylamide (LDA) produced lithium enolate of <I>O</I>-ethyl <I>S</I>-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate, which reacted with an aldehyde to afford exclusively (<I>E</I>)-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, (<I>Z</I>)-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.

• 公益社団法人 日本化学会の論文

著者

• Matsui Syuichi

  Department of Industrial Chemistry, Fukui Technical College

関連論文

• Stereoselective synthesis of (E)-or (Z)-.ALPHA.-alkylidene-.GAMMA.-butyrolactone from .GAMMA.-butyrolactone and bis[ethoxy(thiocarbonyl)] disulfide and mechanistic studies of the effect of metal complexes on the stereoselection.

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