Asymmetrische Synteese. III. Versuch zur Darstellung eines optisch-aktiven Amins durch die Reduktion des Ketoxims beim Vorhandensein von optisch-aktiver Säure

Nakamura, Yozo

doi:10.1246/bcsj.16.367

Cited by 21 publications

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“…adsorption of tartaric acid on Ni. [69][70] In this case, the incoming prochiral molecules interact with the supramolecular structure as a whole, e.g. by adsorbing in chiral "pockets".…”

Section: Discussionmentioning

confidence: 99%

“…Generally, imposing chirality to surface processes can be performed in two different ways: (i) formation of chiral supramolecular structures, such as, for example, adsorption of tartaric acid on Ni. 69,70 In this case, the incoming prochiral molecules interact with the supramolecular structure as a whole, for example by adsorbing in chiral "pockets". (ii) The second way is adsorption of chiral modifiers, which form 1:1 complexes with the prochiral reactants.…”

Section: The Journal Of Physical Chemistry Lettersmentioning

confidence: 99%

“…In this type of catalysis, the surfaces are modified by adsorption of chiral adsorbates, exhibiting enantiospecific interaction with a pro-chiral reactant, which directs the catalytic process toward formation of only one enantiomeric form of the product. Generally, imposing chirality to surface processes can be performed in two different ways: (i) formation of chiral supramolecular structures, such as, for example, adsorption of tartaric acid on Ni. , In this case, the incoming prochiral molecules interact with the supramolecular structure as a whole, for example by adsorbing in chiral “pockets”. (ii) The second way is adsorption of chiral modifiers, which form 1:1 complexes with the prochiral reactants.…”

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confidence: 99%

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Partial Hydrogenation of Unsaturated Carbonyl Compounds: Toward Ligand-Directed Heterogeneous Catalysis

Schauermann

2018

J. Phys. Chem. Lett.

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In this Perspective, we report on the recent progress in atomistic-level understanding of selective partial hydrogenation of α,β-unsaturated carbonyl compounds, particularly acrolein, toward unsaturated alcohols over model single crystalline and nanostructured Pd catalysts. This reaction was observed to proceed with nearly 100% selectivity over Pd(111) but not over supported Pd nanoparticles. The origin of the high selectivity was related to formation of a dense overlayer of oxopropyl surface species occurring at the early reaction stages via partial hydrogenation of the C=C bond in acrolein with only one H atom. This oxopropyl overlayer strongly modifies the adsorption and reactive properties of Pd(111), turning it 100% selective toward C=O bond hydrogenation. The underlying reaction mechanism represents a particular case of ligand-directed heterogeneous catalysis, in which the surface adsorbates do not directly participate in the catalytic process as the reaction intermediates but strongly affect the elementary reaction steps via specific adsorbate-adsorbate interactions.

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“…adsorption of tartaric acid on Ni. [69][70] In this case, the incoming prochiral molecules interact with the supramolecular structure as a whole, e.g. by adsorbing in chiral "pockets".…”

Section: Discussionmentioning

confidence: 99%

Section: The Journal Of Physical Chemistry Lettersmentioning

confidence: 99%

mentioning

confidence: 99%

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Partial Hydrogenation of Unsaturated Carbonyl Compounds: Toward Ligand-Directed Heterogeneous Catalysis

Schauermann

2018

J. Phys. Chem. Lett.

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Catalytic Asymmetric Hydrogenation of C  N Functions

Blaser¹,

Spindler²

2009

Organic Reactions

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Chiral amines are important targets for synthetic chemists and attempts to prepare such compounds via enantioselective hydrogenation of an appropriate CN function date back to 1941. Originally, only heterogeneous hydrogenation catalysts such as Pt black, Pd/C, or Raney nickel were employed. Remarkable progress has been made since the 1990s and a variety of very selective catalysts are now available for the enantioselective reduction of different types of CN functions. The first industrial application was announced in 1996. Despite progress, the enantioselective hydrogenation of prochiral CN groups such as imines, oximes, or hydrozones is still a challenge. This chapter provides a comprehensive overview of the enantioselective hydrogenation and transfer hydrogenation of various CN functions using chiral catalysts. Because the net transformation is the same for both types, the results of various substrate types are summarized together. In many cases, different catalyst types are required. For example, if hydrogen is used, the metal must be able to activate the very strong HH bonds, In contrast, the activation seems to be more facile for the transfer of donor molecules such as formic acid and Hantzch esters, which form aromatic products. This review covers the literature up to September 2007.

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Catalytic Hydrogenation and Dehydrogenation

Sheldon

Bekkum

2000

Fine Chemicals Through Heterogeneous Catalysis

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Asymmetrische Synteese. III. Versuch zur Darstellung eines optisch-aktiven Amins durch die Reduktion des Ketoxims beim Vorhandensein von optisch-aktiver Säure

Abstract: Die Reduktion des asymmetrischenKetoxims (I)ergab im allgemeinen ein Amin von Formel (II), welches ein asymmetrisches C-Atom enthalt. Somit durfen wir das Amin in seine opt. Antipoden zerlegen.(1) Diese Mitteil. wurde schon auf Japanisch berichtet,

Cited by 21 publications

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Partial Hydrogenation of Unsaturated Carbonyl Compounds: Toward Ligand-Directed Heterogeneous Catalysis

Partial Hydrogenation of Unsaturated Carbonyl Compounds: Toward Ligand-Directed Heterogeneous Catalysis

Catalytic Asymmetric Hydrogenation of C  N Functions

Catalytic Hydrogenation and Dehydrogenation

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