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Selective Synthesis of Spirooxindoles by an Intramolecular Heck-Mizoroki Reaction
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.ORCID iD: 0000-0002-2885-2016
AstraZeneca, Dept Med Chem Cardiovasc & Metab Dis, Innovat Med & Early Dev Biotech Unit, Pepparedsleden 1, S-43183 Molndal, Sweden..
AstraZeneca, Dept Med Chem Cardiovasc & Metab Dis, Innovat Med & Early Dev Biotech Unit, Pepparedsleden 1, S-43183 Molndal, Sweden..
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2017 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 10, p. 2738-2741Article in journal (Refereed) Published
Abstract [en]

We report a highly diastereoselective synthesis of cydopentene-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.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2017. Vol. 19, no 10, p. 2738-2741
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Organic Chemistry
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URN: urn:nbn:se:uu:diva-326242DOI: 10.1021/acs.orglett.7b01094ISI: 000402023500071PubMedID: 28471686OAI: oai:DiVA.org:uu-326242DiVA, id: diva2:1130546
Available from: 2017-08-10 Created: 2017-08-10 Last updated: 2017-08-10Bibliographically approved

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Roy, TamalBrandt, PeterSävmarker, JonasLarhed, Mats

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