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Rhodium phosphine-phosphite catalysts in the hydrogenation of challenging N-(3,4-dihydronaphthalen-2-yl) amide derivatives

 

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Opened Access Rhodium phosphine-phosphite catalysts in the hydrogenation of challenging N-(3,4-dihydronaphthalen-2-yl) amide derivatives
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Author: Arribas Nieto, Inmaculada
Rubio Moreno, Miguel
Kleman, Patryk Artur
Pizzano Mancera, Antonio
Date: 2013
Published in: Journal of Organic Chemistry, 78, 3997-4005.
Document type: Article
Abstract: 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.
Cite: Arribas Nieto, I., Rubio Moreno, M., Kleman, P.A. y Pizzano Mancera, A. (2013). Rhodium phosphine-phosphite catalysts in the hydrogenation of challenging N-(3,4-dihydronaphthalen-2-yl) amide derivatives. Journal of Organic Chemistry, 78, 3997-4005.
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URI: https://hdl.handle.net/11441/70327

DOI: 10.1021/jo400345v

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