Enantioselective Folding of Enynes by Gold(I) Catalysts with a Remote C2-Chiral Element
Chiral gold(I) catalysts have been designed based on a modi-fied JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cycliza-tions of 1,6-enynes. These chiral mononuclear catalysts h...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2017 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/522470 |
| Acceso en línea: | http://hdl.handle.net/2072/522470 https://doi.org/10.1021/jacs.9b06326 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | Chiral gold(I) catalysts have been designed based on a modi-fied JohnPhos ligand with a distal C2-2,5-diarylpyrrolidine that creates a tight binding cavity. The C2-chiral element is close to where the C-C bond formation takes place in cycliza-tions of 1,6-enynes. These chiral mononuclear catalysts have been applied for the enantioselective 5-exo-dig and 6-endo-dig cyclization of different 1,6-enynes as well as in the first enan-tioselective total synthesis of three members of the carexane family of natural products. Opposite enantioselectivities have been achieved in seemingly analogous reactions of 1,6-enynes, which result from different chiral folding of the substrates based on attractive aryl-aryl interactions. |
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