Cu-Fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides |
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| Authors: | Silvia Cabrera Belén Martín-Matute Juan C Carretero |
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| Institution: | a Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
b Kimika Fakultatea, Euskal Herriko Unibertsitatea, P.K. 1072, San Sebastián-Donostia, Spain |
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| Abstract: | The CuI-Fesulphos catalyst system (≤3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity (69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed. |
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| Keywords: | 1 3-Dipolar cycloaddition Azomethine ylide Asymmetric catalysis Chiral ligand Copper Enantioselectivity Dipolarophile |
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