An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel-Crafts/Michael/Michael/Aldol Condensation Sequence
| Autor: | Dieter Enders, Lars Fritze, Nico Erdmann, Arne R. Philipps |
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| Rok vydání: | 2016 |
| Předmět: |
Trimethylsilyl
Stereochemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Article Stereocenter chemistry.chemical_compound Cascade reaction domino reaction organocatalysis alkenylation Enantiomeric excess Friedel–Crafts reaction 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis asymmetric catalysis 3. Good health 0104 chemical sciences quadruple cascade Organocatalysis ddc:540 Aldol condensation |
| Zdroj: | Synthesis Synthesis 47(16), 2377-2384 (2015). doi:10.1055/s-0034-1380197 |
| ISSN: | 0039-7881 |
| DOI: | 10.1055/s-0034-1380197 |
| Popis: | An organocatalytic quadruple cascade initiated by a Friedel–Crafts-type reaction is described. The (S)-diphenylprolinol trimethylsilyl ether catalyzed reaction yields highly functionalized cyclohexenecarbaldehydes bearing a 1,1-bis[4-(dialkylamino)phenyl]ethene moiety and three contiguous stereogenic centers. The reaction tolerates various functional groups and all products are obtained with very good diastereoselectivity and with virtually complete enantiomeric excess. Graphical Abstract |
| Databáze: | OpenAIRE |
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