ol7b01094_si_001.pdf (7.57 MB)
Selective Synthesis of Spirooxindoles by an Intramolecular Heck–Mizoroki Reaction
journal contribution
posted on 2017-05-04, 15:35 authored by Tamal Roy, Peter Brandt, Alexander Wetzel, Joakim Bergman, Jonas Brånalt, Jonas Sävmarker, Mats LarhedWe 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.