Selective Synthesis of Spirooxindoles by an Intramolecular Heck-Mizoroki Reaction.

Roy T, Brandt P, Wetzel A, Bergman J, Brånalt J, Sävmarker J, Larhed M

Org. Lett. 19 (10) 2738-2741 [2017-05-19; online 2017-05-04]

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.

Affiliated researcher

PubMed 28471686

DOI 10.1021/acs.orglett.7b01094

Crossref 10.1021/acs.orglett.7b01094

Publications 9.5.0