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
作者:Syuichi Matsui
DOI:10.1246/bcsj.60.1853
日期:1987.5
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