Highly Enantioselective Rhodium-Catalyzed Hydrogenation with Monodentate Ligands

Berg, Michel van den; Minnaard, Adriaan J.; Schudde, Ebe P.; Esch, Jan H. van; Vries, André H.M. de; Vries, Johannes G. de; Feringa, Bernard

doi:10.1021/ja002507f

Cited by 442 publications

(201 citation statements)

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“…The hydrogenation catalyzed by a [2.2]PHANEPHOS-Rh complex 33 (see Figure 1.2) is also suggested to proceed through the dihydride/unsaturate mechanism. 34 Chiral monodentate phosphites 35,36 and phosphoramidites 37,38 are also effective ligands for Rh-catalyzed asymmetric hydrogenation of enamide substrates. As seen in the structure of MonoPhos 37,38 illustrated in Figure 1.2, combination of the modified BINOL backbone and the amine part gives a structural variety to this type of ligand.…”

mentioning

confidence: 99%

Ligand Design for Catalytic Asymmetric Reduction

Ohkuma¹,

Kitamura²,

Noyori³

2006

New Frontiers in Asymmetric Catalysis

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confidence: 99%

Ligand Design for Catalytic Asymmetric Reduction

Ohkuma¹,

Kitamura²,

Noyori³

2006

New Frontiers in Asymmetric Catalysis

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“…11 We have also recently reported the asymmetric hydrogenation of 2,6-substituted quinolines 12 using an iridium catalyst with the monodentate phosphoramidite ligand (S)-PipPhos L1a, with excellent conversions and ee's. Phosphoramidites have the advantage of being readily accessible, highly diverse, air stable, and inexpensive compared to most bidentate ligands.…”

mentioning

confidence: 94%

Asymmetric hydrogenation of 2-substituted N-protected-indoles catalyzed by rhodium complexes of BINOL-derived phosphoramidites

Mrsic

Jerphagnon

Minnaard

et al. 2010

Tetrahedron: Asymmetry

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Asymmetric hydrogenation of 2-substituted N-protected-indoles catalyzed by rhodium complexes of BINOL-derived phosphoramidites Mršić, Nataša; Jerphagnon, Thomas; Minnaard, Adriaan; de Vries, Johannes G.; Mrsic, N.; Feringa, B.L. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. The rhodium-catalyzed asymmetric hydrogenation of 2-substituted N-protected-indoles using monodentate phosphoramidites as ligands was examined. Full conversion and 74% ee, were obtained with a catalyst based on PipPhos. The use of a catalytic amount of base is necessary for activity; best results were obtained with Cs 2 CO 3 .

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“…Monophosphines R * PPh 2 , where R * is a chiral group, were less successful [15]. It was only in 2000 that it was discovered that some phosphorus ligands such as (RO) 2 PNR 2 or (RO) 2 POR' are excellent ligands for asymmetric hydrogenation [16,17].…”

Section: Introductionmentioning

confidence: 99%

Nonlinear Effects in Enantioselective Organometallic Catalysis

Kagan

2007

Oil & Gas Science and Technology - Rev. IFP

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*Dedicated to Yves Chauvin for his outstanding contributions to catalysis Ce manuscrit est dédié à Yves Chauvin pour ses contributions exceptionnelles à la catalyse Résumé -Effets nonlinéaires dans la catalyse organométallique énantiosélective -L'historique de la catalyse organométallique énantiosélective est rappelé en introduction. Les problèmes liés à l'emploi d'auxiliaires chiraux énantioimpurs sont discutés, les effets nonlinéaires sont définis et des modèles mathématiques simples sont présentés. De nombreux exemples d'effets nonlinéaires positifs ou négatifs sont maintenant connus, certains sont mentionnés. Les effets nonlinéaires sont utiles pour aborder des mécanismes réactionnels. L'amplification asymétrique peut avoir des applications en catalyse, en permettant d'utiliser un ligand qui n'est pas énantiopur. Abstract -Nonlinear Effects in Enantioselective Organometallic

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Highly Enantioselective Rhodium-Catalyzed Hydrogenation with Monodentate Ligands

Cited by 442 publications

References 35 publications

Ligand Design for Catalytic Asymmetric Reduction

Ligand Design for Catalytic Asymmetric Reduction

Asymmetric hydrogenation of 2-substituted N-protected-indoles catalyzed by rhodium complexes of BINOL-derived phosphoramidites

Nonlinear Effects in Enantioselective Organometallic Catalysis

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