Pd-catalyzed [3+2] cycloaddition between carbon dioxide and (2-(acetoxymethyl)-1-buten-3-yl)trimethylsilane

CHED 312

Amanda D. Worthy, aworthy@goucher.edu and George E. Greco, ggreco@goucher.edu. Department of Chemistry, Goucher College, 1021 Dulaney Valley Road, Baltimore, MD 21204
The Pd-catalyzed [3+2] cycloaddition between carbon dioxide and (2-(acetoxymethyl)-1-buten-3-yl)trimethylsilane under mild conditions produces 3,4-dimethyl-2(5H)-furanone regioselectively. This substrate is more reactive than the parent substrate (without the methyl group), but also more prone to undesired side reactions. The synthesis of the substrate and efforts towards optimization of the cycloaddition reaction will be presented.