Enantioselective Rh-Catalyzed Hydrogenation of <i>N</i>-Formyl Dehydroamino Esters with Monodentate Phosphoramidite Ligands

Panella, Lavinia; Aleixandre, AM; Kruidhof, GJ; Robertus, Jort; Vries, Johannes G. de; Minnaard, Adriaan J.; Aleixandre, Alicia Marco; Kruidhof, Gerlof J.; Feringa, Bernard

doi:10.1021/jo052451d

Cited by 65 publications

(45 citation statements)

References 87 publications

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“…Commonly, homogeneous imine hydrogenation catalysts are Ir and Rh complexes and require relative high H 2 pressures. [138,139] There is an incentive to develop heterogeneous, highly active catalysts based on less expensive metals that work under lower hydrogen pressures. Corma and co-workers have reported chiral palladium-and nickel-salen complexes covalently anchored to a series of silica supports that are able to effect the hydrogenation of imines at 4 bar.…”

Section: The Anchored [Sncl 5 ]mentioning

confidence: 99%

Silica‐Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis

2006

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Very frequently the most costly components in a chemical reaction are not the starting materials or the reaction products, but the catalyst. In addition to the advantages from the economic point of view, recovery and reuse of the catalyst is equally important in order to avoid wastes, so improving the greenness of the process. There is a current tendency to transform homogeneous into heterogeneous catalysis, that will even be accelerated in the near future. Starting from a successful homogeneous catalyst, one general methodology allowing its recovery and reuse is to immobilize a suitable derivative of the active catalyst on an insoluble solid support. When the catalyst does not deactivate and is sufficiently stable under the reaction conditions, the ultimate immobilization methodology is to attach covalently the catalytically active species to the support. In this contribution, after introducing some general principles describing the fundamentals of the covalent anchoring, the emphasis is placed more on giving an overview of the most important types of covalently anchored catalysts, including Brçnsted and Lewis acids, covalently anchored bases and hydrogenation complexes. Hot topics such as silica-bound organocatalysts and the application of periodic mesoporous organosilicas as heterogeneous catalysts is also covered.

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Section: The Anchored [Sncl 5 ]mentioning

confidence: 99%

Silica‐Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis

2006

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“…[9d, 25,26] The latter effect has been attributed to hydrogen bonds, but since phosphoramidite D2 is immobilised on a polymeric support, which restricts the occurrence of these interactions, our data indicate that other factors also play a role. [26] Nonsupported rhodium species may contribute to the activity of the in situ formed catalysts and as a result will lower the overall enantioselectivity.…”

Section: Rhodium-catalysed Hydrogenationmentioning

confidence: 82%

Supported Chiral Monodentate Ligands in Rhodium‐Catalysed Asymmetric Hydrogenation and Palladium‐Catalysed Asymmetric Allylic Alkylation

et al. 2009

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A family of monodentate polystyrene-supported phosphites, phosphoramidites and phosphanes has been prepared and evaluated as ligands in rhodium-catalysed asymmetric hydrogenation and palladium-catalysed asymmetric allylic alkylation. The supported ligands yielded active and enantioselective catalysts, which in selected cases match the performance of the nonsupported counterparts. As expected, the performance of the supported ligands in the rhodium-catalysed hydrogenation depends on the nature of the ligand, the type of polymeric support, as well as on the substrate. Ad-

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“…(4)]. [22] The copper(I) salts CuCl and Cu 2 O, were found to be more efficient than either t -BuOK or ZnCl 2 , providing a direct comparison of catalytic and non-catalytic methods.…”

Section: Aldol-type Condensationsmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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Enantioselective Rh-Catalyzed Hydrogenation of N-Formyl Dehydroamino Esters with Monodentate Phosphoramidite Ligands

Cited by 65 publications

References 87 publications

Silica‐Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis

Silica‐Bound Homogenous Catalysts as Recoverable and Reusable Catalysts in Organic Synthesis

Supported Chiral Monodentate Ligands in Rhodium‐Catalysed Asymmetric Hydrogenation and Palladium‐Catalysed Asymmetric Allylic Alkylation

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

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