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Stereodivergent Synthesis of Trisubstituted Enamides: Direct Access to Both Pure Geometrical Isomers
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8431-6368
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 62019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 21, p. 13540-13548Article in journal (Refereed) Published
Abstract [en]

A stereodivergent strategy has been developed to access either (E)- or (Z)-isomers of trisubstituted enamides. Starting from an extensive range of ketones, it was possible to synthesize and isolate the desired pure isomer by switching the reaction conditions. Lewis acid activation enables the formation of the (E)-isomers in high stereoselectivity (>90:10) and good yields. On the other hand, the use of a Bronsted acid allows the preparation of the (Z)-isomers, again in high selectivity (up to 99:1), with moderate yields.

Place, publisher, year, edition, pages
2019. Vol. 84, no 21, p. 13540-13548
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Chemical Sciences
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URN: urn:nbn:se:su:diva-176596DOI: 10.1021/acs.joc.9b01803ISI: 000494562600028PubMedID: 31532658OAI: oai:DiVA.org:su-176596DiVA, id: diva2:1376972
Available from: 2019-12-10 Created: 2019-12-10 Last updated: 2019-12-10Bibliographically approved

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Massaro, LucaYang, JianpingKrajangsri, SuppachaiSilvi, EmanueleAndersson, Pher G.
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