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Selective Synthesis of Spirooxindoles by an Intramolecular Heck–Mizoroki Reaction

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journal contribution
posted on 04.05.2017 by Tamal Roy, Peter Brandt, Alexander Wetzel, Joakim Bergman, Jonas Brånalt, Jonas Sävmarker, Mats Larhed
We report a highly diastereoselective synthesis of cyclopentene–spirooxindole derivatives via an intramolecular Heck–Mizoroki reaction using aryl bromides as precursors. The reactions were performed under dry conditions or in a DMF–water system. This protocol can be useful to introduce several functionalities to the aromatic nucleus of the spirooxindoles. DFT calculations were performed to rationalize the high antiselectivity. A functionalized spiroproduct was transformed into a cyclic amino acid derivative.