Synthesis of Antitricyclic Morpholine Derivatives through Iodine(III)-Mediated Intramolecular Umpolung Cycloaddition of Olefins

A (diacetoxyiodo)benzene-mediated intramolecular cycloaddition of olefins to construct tricyclic morpholines is presented. A series of substituted tricyclic morpholines were obtained in one-step simple operation under mild conditions, and the NMR studies were employed to see the interaction of reactants. The studies on stereochemistry showed that transformation of Z-alkene was inhibited, which is interpreted by density functional theory calculations on Z- and E-transition state models, and only E-alkene resulted in an anticycloaddition product, which is testified by a single-crystal X-ray diffraction analysis.