Stereoselective Sequential Diels-Alder Reactions on a Cyclic Furan Trimer for the Construction of an Asymmetric
Kenta Komatsu1, Arseni Kostenko2, Shigeyoshi Inoue2
1School of Science and Engineering, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Abstract:
Multiple Diels-Alder reactions are a powerful method to construct large asymmetric scaffolds, but these reactions often produce numerous isomers. We now report a triple Diels-Alder reaction between a cyclic furan trimer and N-substituted maleimides, achieving selective synthesis of a single asymmetric tris-adduct. The stereoselectivity of cycloaddition to π-extended furan derivatives was clarified by the experimental analysis of intermediates and theoretical calculations. Furthermore, the potential of the method to synthesize a chiral, optically active molecule was demonstrated.
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