Organic Letters
Organic Letters
5 years ago

Selective Synthesis of Spirooxindoles by an Intramolecular Heck–Mizoroki Reaction

Selective Synthesis of Spirooxindoles by an Intramolecular Heck–Mizoroki Reaction
Alexander Wetzel, Tamal Roy, Peter Brandt, Jonas Brånalt, Jonas Sävmarker, Mats Larhed, Joakim Bergman
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01094

DOI: 10.1021/acs.orglett.7b01094

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