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New C2-Symmetric Diphosphite Ligands Derived from Carbohydrates: Effect of the Remote Stereocenters on Asymmetric Catalysis

The synthesis of new modular chiral diphosphite ligands with C2-symmetry and carbohydrate backbone is reported. We also report here the synthesis of the corresponding rhodium complexes [Rh(COD)(L)]BF4 (L=diphosphite). All these species have been characterised in solution by NMR spectroscopy and in some cases in the solid state by X-ray diffraction. The solution structures of the hydridorhodiumcarbonyl species [RhH(CO)2(L)], where L=diphosphites 12a14a, 12b, have been studied using high-pressure NMR spectroscopy. The configuration and substitution of the remote stereocentres in positions 2 and 5 of the tetrahydrofuran ring of the diphosphite ligands were observed to have a considerable influence on the results obtained in the rhodium-catalysed hydroformylation and hydrogenation reactions. Thus, the configuration of the major isomer obtained in the hydroformylation reaction may be controlled by changing the configuration of these stereocentres.

New C2-symmetric diphosphite ligands derived from carbohydrates: Effect of the remote stereocenters on asymmetric catalysis

M. R. Axet, J. Benet-Buchholz, C. Claver, S. Castillón

Adv. Synth. Catal. 2007, 349, 1983-1998
DOI: Go to the journal

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