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Title

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

AuthorsArribas, Inmaculada ; Rubio, Miguel ; Kleman, Patryk Artur; Pizzano, Antonio
Issue Date2013
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 78: 3997- 4005 (2013)
AbstractThe 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.
URIhttp://hdl.handle.net/10261/97634
DOIhttp://dx.doi.org/10.1021/jo400345v
Identifiersdoi: 10.1021/jo400345v
issn: 0022-3263
Appears in Collections:(IIQ) Artículos
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