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Título: | Rhodium phosphine-phosphite catalysts in the hydrogenation of challenging N-(3,4-dihydronaphthalen-2-yl) amide derivatives |
Autor: | Arribas, Inmaculada CSIC; Rubio, Miguel CSIC ORCID; Kleman, Patryk Artur; Pizzano, Antonio CSIC ORCID | Fecha de publicación: | 2013 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 78: 3997- 4005 (2013) | Resumen: | The enantioselective catalytic hydrogenation of N-(3,4-dihydronaphthalen-2- yl) amides (1) with rhodium catalysts bearing phosphine-phosphite ligands 4 has been studied. A wide catalyst screening, facilitated by the modular structure of 4, has found a highly enantioselective catalyst for this reaction. This catalyst gives a 93% ee in the hydrogenation of 1a and also produces high enantioselectivities, ranging from 83 to 93% ee, in the hydrogenation of several OMe- and Br-substituted substrates. In contrast, the structurally related enol esters 2 are very reluctant to undergo hydrogenation. A coordination study of the representative enamide 1d has shown an unusual η6-arene coordination mode, over the typical O,C,C chelating mode for enamides, as the preferred one for this substrate in a Rh(I) complex. Deuteration reactions of 1c,d indicate a clean syn addition of deuterium to the double bond without an isotopic effect on the enantioselectivity. © 2013 American Chemical Society. | URI: | http://hdl.handle.net/10261/97634 | DOI: | 10.1021/jo400345v | Identificadores: | doi: 10.1021/jo400345v issn: 0022-3263 |
Aparece en las colecciones: | (IIQ) Artículos |
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Enamide_H2_CSIC-repository.pdf | 303,69 kB | Adobe PDF | Visualizar/Abrir |
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