TY - DATA T1 - Selective Synthesis of Spirooxindoles by an Intramolecular Heck–Mizoroki Reaction PY - 2017/05/04 AU - Tamal Roy AU - Peter Brandt AU - Alexander Wetzel AU - Joakim Bergman AU - Jonas Brånalt AU - Jonas Sävmarker AU - Mats Larhed UR - https://acs.figshare.com/articles/journal_contribution/Selective_Synthesis_of_Spirooxindoles_by_an_Intramolecular_Heck_Mizoroki_Reaction/4970753 DO - 10.1021/acs.orglett.7b01094.s001 L4 - https://ndownloader.figshare.com/files/8360759 KW - DMF KW - spirooxindole KW - Spirooxindole KW - intramolecular KW - functionalized spiroproduct KW - cyclopentene KW - derivative KW - DFT calculations KW - functionalitie KW - Heck KW - nucleus KW - diastereoselective synthesis KW - acid KW - antiselectivity KW - precursor KW - cyclic KW - aryl bromides KW - Intramolecular KW - Selective Synthesis N2 - 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. ER -