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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Selective Synthesis of Spirooxindoles by an Intramolecular Heck-Mizoroki Reaction
Tamal Roy1, Peter Brandt1, Alexander Wetzel2
1Department of Medicinal Chemistry, BMC, Uppsala University , Box 574, SE-751 23 Uppsala, Sweden.
Abstract:
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.
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