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(g) Hoen, R.; Boogers, J. A. F.; Bernsmann, H.; Minnaard, A. J.; Meetsma, A.; Tiemersma-Wegman, T. D.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Angew. Chem., Int. Ed. 2005, 44, 4209.
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For other representative phosphine-phosphoramidite ligands in hydrogenation, see: a
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For other representative phosphine-phosphoramidite ligands in hydrogenation, see: (a) Francio, G.; Faraone, F.; Leitner, W. Angew. Chem., Int. Ed. 2000, 39, 1428.
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16
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33846937470
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So far, we have not been able to obtain a suitable single crystal of Rh/1 for the X-ray diffraction experiment. However, the structure of an isoelectronic Pd(II) complex may provide valuable coordination information as well. See, for example: Bayer, A.; Murszat, P.; Thewalt, U.; Rieger, B. Eur. J. Inorg. Chem. 2002, 2614.
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So far, we have not been able to obtain a suitable single crystal of Rh/1 for the X-ray diffraction experiment. However, the structure of an isoelectronic Pd(II) complex may provide valuable coordination information as well. See, for example: Bayer, A.; Murszat, P.; Thewalt, U.; Rieger, B. Eur. J. Inorg. Chem. 2002, 2614.
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(a) van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.
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(b) Berg, M. v. d.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schedde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Maljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308.
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Meetsma, A.6
Feringa, B.L.7
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Maljaars, C.E.P.9
Williams, C.E.10
Hyett, D.11
Boogers, J.A.F.12
Henderickx, H.J.W.13
de Vries, J.G.14
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(c) Bernsmann, H.; Berg, M. v. d.; Hoen, R.; Minnaard, A. J.; Mehler, G.; Reetz, M. T.; de Vries, J. G.; Feringa, B. L. J. Org. Chem. 2005, 70, 943.
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Reetz, M.T.6
de Vries, J.G.7
Feringa, B.L.8
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(d) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wana, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480.
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(e) Wu, S.; Zhang, W.; Zhang, Z.; Zhang, X. Org. Lett. 2004, 6, 3565.
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25
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Aware of this issue, our group recently developed DuanPhos as both enantiomers compared with the previously reported TangPhos, which exists as only one enantiomer. See
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Aware of this issue, our group recently developed DuanPhos as both enantiomers compared with the previously reported TangPhos, which exists as only one enantiomer. See: Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646.
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(2005)
Eur. J. Org. Chem
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Liu, D.1
Zhang, X.2
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26
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20444466430
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In heterogeneous hydrogenation, reversal of enantioselectivity is under active study. See, for example
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(a) In heterogeneous hydrogenation, reversal of enantioselectivity is under active study. See, for example: Bonalumi, N.; Vargas, A.; Ferri, D.; Burgi, T.; Mallat, T.; Baiker, A. J. Am. Chem. Soc. 2005, 127, 8467.
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Bonalumi, N.1
Vargas, A.2
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Mallat, T.5
Baiker, A.6
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In asymmetric transfer hydrogenation, it was shown very recently that a subtle change in ligand structure can result in a switch of the product's absolute configurations. See: Zaitsev, A. B, Adolfsson, H. Org. Lett. 2006, 8, 5129
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(b) In asymmetric transfer hydrogenation, it was shown very recently that a subtle change in ligand structure can result in a switch of the product's absolute configurations. See: Zaitsev, A. B.; Adolfsson, H. Org. Lett. 2006, 8, 5129.
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A Rh complex of an α-glucosidic bisphosphinite ligand gave 73% ee (S) in ethanol but 6% ee (R) in benzene during the hydrogenation of dehydroamino esters. See: Selke, R. J. Prakt. Chem. 1987, 329, 717.
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(a) A Rh complex of an α-glucosidic bisphosphinite ligand gave 73% ee (S) in ethanol but 6% ee (R) in benzene during the hydrogenation of dehydroamino esters. See: Selke, R. J. Prakt. Chem. 1987, 329, 717.
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2 but 26% ee (S) in MeOH during the hydrogenation of an enol acetate. See: Panella, L.; Feringa, B. L.; de Vires, J. G.; Minnaard, A. J. Org. Lett. 2005, 7, 4177.
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2 but 26% ee (S) in MeOH during the hydrogenation of an enol acetate. See: Panella, L.; Feringa, B. L.; de Vires, J. G.; Minnaard, A. J. Org. Lett. 2005, 7, 4177.
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2·1a, the distance from P(3) to P(2) is 3.906 Å, from P(3) to N(1) is 3.779 Å, and from P(3) to Pd(1) is 5.499 Å.
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2·1a, the distance from P(3) to P(2) is 3.906 Å, from P(3) to N(1) is 3.779 Å, and from P(3) to Pd(1) is 5.499 Å.
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