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Accelerating Amine-Catalyzed Asymmetric Reactions by Intermolecular Cooperative Thiourea/Oxime Hydrogen-Bond Catalysis
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5108-6487
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
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2021 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2021, no 21, p. 3043-3049Article in journal (Refereed) Published
Abstract [en]

The ability of intermolecular cooperative thiourea/oxime hydrogen-bond catalysis for improving and accelerating asymmetric aminocatalysis is presented. The two readily available hydrogen-bond-donating catalysts operates in synergy with a chiral amine catalyst to accomplish highly stereoselective transformations. The synergistic catalyst systems simultaneously activate both electrophiles and nucleophiles, and make the transformations more chemo- and stereoselective. This was exemplified by performing co-catalytic enantioselective direct intermolecular α-alkylation reactions of aldehydes, direct aldol reactions, and asymmetric conjugate reactions, which gave the corresponding products in high yields and enantiomeric ratios.

Place, publisher, year, edition, pages
2021. Vol. 2021, no 21, p. 3043-3049
Keywords [en]
Asymmetric catalysis, Cooperative catalysis, C−C bond formation, Hydrogen-bond-donation, α-Alkylation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-42730DOI: 10.1002/ejoc.202100315ISI: 000674294200014Scopus ID: 2-s2.0-85110506903OAI: oai:DiVA.org:miun-42730DiVA, id: diva2:1583620
Available from: 2021-08-09 Created: 2021-08-09 Last updated: 2025-09-25Bibliographically approved

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Guangning, MaAfewerki, SamsonZhang, KeihangIbrahem, IsmailCordova, Armando

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Guangning, MaAfewerki, SamsonZhang, KeihangIbrahem, IsmailCordova, Armando
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Department of Natural SciencesDepartment of Chemical Engineering
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European Journal of Organic Chemistry
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