Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction |
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Authors: | Vitor A Fernandes Rafaely N Lima Yoisel B Broterson Meire Y Kawamura Radell Echemendía Alexander F de la Torre Marco A B Ferreira Daniel G Rivera Marcio W Paixo |
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Institution: | Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos, São Carlos São Paulo 13565-905 Brazil.; Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Concepción, Concepción Chile ; Faculty of Chemistry, University of Havana, La Habana Cuba |
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Abstract: | An efficient strategy combining the stereocontrol of organocatalysis with the diversity-generating character of multicomponent reactions is described to produce structurally unique, tetrasubstituted cyclopentenyl frameworks. An asymmetric Michael addition–hemiacetalization between α-cyanoketones and α,β-unsaturated aliphatic aldehydes was performed for constructing cyclic hemiacetals, which were next employed as chiral bifunctional substrates in a new diastereoselective intramolecular isocyanide-based multicomponent reaction. This approach furnished a diversity of structurally complex compounds – including peptidomimetics and natural product hybrids in high stereoselectivity (up to >99% ee and up to >99 : 1 dr) and in moderate to high yields.Simple and available reagents are combined in this new three-component isocyanide-based multicomponent reaction providing an interesting and straightforward way to prepare complex and highly functionalized cyclopentenyl rings. |
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