Asymmetric Hydrogenation of Heteroaromatic Compounds

Zhou, Yong‐Gui

doi:10.1021/ar700094b

Cited by 627 publications

(158 citation statements)

References 78 publications

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“…In this study, we proved that 3-substituted benzisoxazoles 1 react with hydrogen in the presence of the chiral ruthenium catalyst, {RuCl(p-cymene)[(R,R)-(S,S)-PhTRAP]}Cl (2). The rutheniumcatalyzed hydrogenation proceeds in the presence of an acylating agent such as Boc 2 O and Cbz-OSu, to afford -substituted N-protected o-hydroxybenzylamines 4-9 in high yields with moderate enantioselectivities.…”

Section: Discussionmentioning

confidence: 78%

“…Before the evaluation of ligands, we attempted the catalytic asymmetric reactions by means of a few in-situ-generated PhTRAP-ruthenium catalysts. In our previous study on the asymmetric hydrogenation of oxazoles, the chiral catalyst was generated in situ from Ru( 3 -methallyl) 2 (cod) and the chiral bisphosphine [30]. However, the chiral ruthenium complex failed to catalyze the conversion of 1a to imine 3a (entry 1).…”

Section: Optimization Of Reaction Conditionsmentioning

confidence: 99%

“…Catalytic asymmetric hydrogenation of heteroaromatics is an important issue in synthetic organic chemistry [1][2][3][4]. The reaction offers a straightforward access to optically active heterocycles, which are seen in various medicines as well as natural products.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Ikeda

Kuwano

2012

Molecules

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A variety of 3-substituted benzisoxazoles were reduced with hydrogen using the chiral ruthenium catalyst, {RuCl(p-cymene)[(R,R)-(S,S)-PhTRAP]}Cl. The ruthenium-catalyzed hydrogenation proceeded in high yield in the presence of an acylating agent, affording -substituted o-hydroxybenzylamines with up to 57% ee. In the catalytic transformation, the N-O bond of the benzisoxazole substrate is reductively cleaved by the ruthenium complex under the hydrogenation conditions. The C-N double bond of the resulting imine is saturated stereoselectively through the PhTRAP-ruthenium catalysis. The hydrogenation produces chiral primary amines, which may work as catalytic poisons, however, the amino group of the hydrogenation product is rapidly acylated when the reaction is conducted in the presence of an appropriate acylating agent, such as Boc 2 O or Cbz-OSu.

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Section: Discussionmentioning

confidence: 78%

Section: Optimization Of Reaction Conditionsmentioning

confidence: 99%

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Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Ikeda

Kuwano

2012

Molecules

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“…Hydroquinoline is structurally essential unit in biologically active natural products [1,2]. The hydroquinoline is widely used as a pharmacophore in drug discovery and exhibits a broad range of biological activities such as anti-HIV, antibacterial, antifungal, antimalarial, antitumor, and cardiovascular effects [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

1,4-Dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde

Kim

2016

Molbank

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“…他们发现手性双亚胺吡啶类型的钴催化剂(22)能够催化偕二取代烯烃的不对称氢化, 并获得了高达 98% ee 的对映选择性 [31] (图 12). [32] . 早期芳香杂环化合物的不对称催化氢化主要集中在取代喹喔啉等含氮杂芳环化合物上, 但成功的例子很少.…”

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New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation

Xie¹,

Zhou²

2012

Acta Chim. Sinica

164

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Chiral transition metal complexes-catalyzed asymmetric hydrogenation is one of the most efficient methods for the synthesis of optically active compounds, and has been intensively investigated in the past decades. This review presents a brief overview on the progress in the transition metal-catalyzed asymmetric hydrogenation since the beginning of this new century from three aspects: (1) chiral ligands and catalysts; (2) new catalytic asymmetric hydrogenations; (3) new methods and new strategies in asymmetric hydrogenations. Chiral monodentate phosphorus ligands have been a renaissance from the beginning of new century, and many efficient chiral monophosphoramidites such as MonoPhos, SiPhos, DpenPhos have been developed. The chiral phosphine ligands with a chirality on the phosphorus atom (P-chirality), such as BenzP*, ZhanPhos, and TriFer, have also been explored. Chiral ligands with a spiro skeleton have been a highlight of design and synthesis of chiral ligands. The chiral spiro ligands such as SDP, SiPhos, SIPHOX, and SpinPHOX are very efficient in asymmetric hydrogenations. The iridium complexes of chiral spiro pyridine-aminophosphine ligands SpiroPAP is the most efficient molecular catalysts up to now with a turnover number (ratio of converted substrate to catalyst) over 4500000 in the hydrogenation of acetophenone. A number of breakthroughs have been made in the researches on new catalytic asymmetric hydrogenations. Highly enantioslective hydrogenations of unprotected enamines, heteroaromatic compounds, and N-H imines have been developed. New methods and strategies including self-assembled, dendrimerized, and ferromagnetic nanomaterials-loaded chiral catalysts with recyclability and reusability, the catalysts with "mixed" chiral ligands have also been successfully applied in the catalytic asymmetric hydrogenations. However, the chiral transition metal complexes catalyzed asymmetric hydrogenation still has many challenges and is looking forward to new breakthroughs in the future. In addition to the continuous developments of new chiral ligands and catalysts with high efficiency, high enantioselectivity, and high chemoselectivity, new strategies such as co-operative or relay catalysis are becoming focuses of the asymmetric hydrogenations studies.

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Asymmetric Hydrogenation of Heteroaromatic Compounds

Cited by 627 publications

References 78 publications

Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

Catalytic Asymmetric Hydrogenation of 3-Substituted Benzisoxazoles

1,4-Dihydro-4-(nitromethyl)-2-phenyl-1-tosylquinoline-3-carbaldehyde

New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation

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