Water-compatible one-pot organocatalytic asymmetric synthesis of cyclic nitrones. Application in intramolecular 1,3-dipolar cycloadditions |
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| Authors: | David Sá dabaIgnacio Delso,Tomá s TejeroPedro Merino |
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| Affiliation: | a Laboratorio de Síntesis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), Universidad de Zaragoza, CSIC, E-50009 Zaragoza, Aragon, Spain
b NMR Service, Centro de Química y Materiales de Aragón (CEQMA), University of Zaragoza, CSIC, E-50009 Zaragoza, Aragon, Spain |
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| Abstract: | Optically active five-membered cyclic nitrones are readily obtained in a one-pot procedure via the organocatalytic Michael addition of aldehydes to nitroolefins and in situ reductive cyclization. Application of the methodology to the synthesis of tricyclic compounds through intramolecular 1,3-dipolar cycloaddition reactions (DFT calculations have also been performed) is also demonstrated. All the reactions were carried out in water as a solvent and excellent ee values (ee >99%) were obtained. |
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| Keywords: | Nitrones Intramolecular dipolar cycloaddition Pyrrolidines Michael addition Organocatalysis |
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