Synergistic Catalysis: Highly Enantioselective Cascade Reaction for the Synthesis of Dihydroacridines
| Autor: | Marta Meazza, Ramon Rios, Tomás Tejero, Sara Meninno, Jung Woon Yang, Pedro Merino‐Gomez |
|---|---|
| Přispěvatelé: | Engineering and Physical Sciences Research Council (UK), Ministerio de Economía y Competitividad (España), European Commission, Gobierno de Aragón, Accademia Nazionale dei Lincei |
| Rok vydání: | 2019 |
| Předmět: |
Enantioselective
010405 organic chemistry Diastereoselective Organic Chemistry education Enantioselective synthesis Iminium General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis humanities 0104 chemical sciences Lewis acid catalysis chemistry.chemical_compound Synergistic catalysis chemistry Cascade reaction Acridine Stereoselectivity acridine diastereoselective enantioselective synergistic catalysis ytterbium Ytterbium |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 1521-3765 |
| Popis: | The first stereoselective synthesis of dihydroacridines through synergistic catalysis, achieving the final target compounds with good to excellent yields and good to excellent enantioselectivities and diastereoselectivities, is reported. The synergistic approach consists in the activation of substituted quinolines with a Lewis acid catalyst that react in a cascade fashion with activated enals in the iminium form. Mechanistic calculations support a consecutive Michael-aldol reaction, followed by dehydration. S.M. and R.R. thank Accademia Nazionale dei Lincei for the RSC fellowship. M.M. and R.R. are grateful for EPSRC Core Capability Funding (EP/K039466/1). T.T. and P.M. acknowledge the MINECO and FEDER Program (Madrid, Spain, project CTQ2016-76155-R) and the Gobierno de Aragjn (Zaragoza, Spain. Biological and Computational Chemistry Group. E-34_17R). |
| Databáze: | OpenAIRE |
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