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Metallo - 1,3-dipoles generated in situ from both aryl and aliphatic imines of α-amino esters by the action of silver salts and tertiary amines undergo cycloaddition at room temperature to 5R-(1 R, 2 S, 5 R-menthyloxyl) - 2(5H)-furanone and to N-acetyl-5R-isopropoxy-2(5H)-pyrrolone giving homochiral cycloadducts in good yield in all cases. π-Interaction between the dipolarophile carbonyl group...
Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt...
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