Chiral bidentate aminophosphine ligands: synthesis, coordination chemistry and asymmetric catalysis |
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Authors: | Zijp Eric J van der Vlugt Jarl Ivar Tooke Duncan M Spek Anthony L Vogt Dieter |
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Institution: | Schuit Institute of Catalysis, Laboratory of Homogeneous Catalysis, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, The Netherlands. |
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Abstract: | Chiral aminophosphines Ph2PN(R)(CH2)nN(R)PPh2 1-4 n= 2, R = CH(CH3)(Ph) 1; n= 3, R = CH(CH2CH3)(Ph) 2, n= 2, R = CH(CH3)(1-naphthyl) 3; n= 2, R = CH(CH3)(C6H11) 4] were synthesized by the reaction of ClPPh2 with the appropriate easily accessible enantiopure amine building blocks. For compounds 1 and 2, the corresponding selenides 5 and 6 were prepared to determine the electronic character of the phosphine moieties. By reaction of 1 with either PdCl2(cod) or PdCl(CH3)(cod) the cis-complexes 7 and 8 were obtained. The molecular structure for complex 7, cis-PdCl2(1)], was determined by X-ray crystallography. Reaction of PtCl2(cod) with 1 or 2 yielded the corresponding monomeric cis-isomers 9 and 10. The rhodium derivative RhCl(CO)(1)] (11) was obtained as a mixture of cis and trans-isomers. Preliminary results in the rhodium catalyzed hydroformylation of styrene and vinyl acetate, with ee's up to 51% and high regioselectivities, showed the potential of these chiral aminophosphines for homogeneous catalysis. |
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