Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Hu, Fangdong; Wei, Yin; Shi, Min; Pindi, Suresh; Li, Guigen

doi:10.1039/c3ob27495k

Cited by 98 publications

(24 citation statements)

References 68 publications

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“…Min Shi et al have developed a highly enantioselective aza-Morita-Baylis-Hillman reaction of isatin imines (1) with methyl vinyl ketones (MVK) 2 catalyzed by β-isocupreidine I and chiral phosphines II (Scheme 75 1). 8 Similar results were obtained affording 3-amino-2-oxindoles 3 bearing a C-3 tetra-substituted stereogenic centre with excellent enantioselectivity (up to 99% ee) and excellent yield up to 98%. In addition to this, the absolute configuration was also found to be same (R) in both cases.…”

Section: Introductionsupporting

confidence: 71%

Stereoselective synthesis of 3-amino-2-oxindoles from isatin imines: new scaffolds for bioactivity evaluation

et al. 2015

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53-Substituted-3-aminooxindoles have attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of number of natural products and drug candidates. The catalytic potential of chiral organocatalysts and metal catalysts has been successfully exploited for the synthesis of enantioenriched 3-amino-2-oxindoles via the addition of various nucleophiles to isatin imines. This review focuses on the catalytic asymmetric synthesis of chiral 3-amino-3-substituted-2-oxindoles.

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Section: Introductionsupporting

confidence: 71%

Stereoselective synthesis of 3-amino-2-oxindoles from isatin imines: new scaffolds for bioactivity evaluation

et al. 2015

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“…The resulting chiral 3-amino-oxindole derivatives were obtained in good to excellent enantioselectivities and overall good yields. It was also noticed that the reaction required a shorter period (48 h), than when compared to the b-isocupreidine organocatalysts (72 h) (Scheme 67 a)) [202]. A similar approach was studied by Zhao et al, but using different acrylates as substrates and a phosphinesquaramide-derived organocatalyst C54.…”

Section: Squaramide and Phosphine Derivativesmentioning

confidence: 97%

Recent advances in the asymmetric catalytic synthesis of chiral 3-hydroxy and 3-aminooxindoles and derivatives: Medicinally relevant compounds

Brandão

Burke

2018

Tetrahedron

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Several oxindole derivatives, of natural or synthetic origin, have been identified as medicinally appealing compounds, with a plethora of bioactivities reported. Chiral 3-hydroxy and 3-aminooxindole scaffolds have captured the attention of several research groups, due to their importance in drug discovery. In this review, we systematically address the wide variety of asymmetric catalytic methodologies employed in the preparation of these relevant chiral scaffolds, present in many biologically active compounds and/or natural products. Special focus will be given to the nature of the catalyst used.

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“…For asymmetric catalytic aza‐Morita–Baylis–Hillman (aza‐MBH) reaction of isatin‐derived ketimines with methyl vinyl ketone see reference 115.…”

Section: Morita–baylis–hillman Reactionsmentioning

confidence: 99%

“…Transformations of cycloalkenones proceed with very good yields under these conditions (Scheme 53). [114] For asymmetric catalytic aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with methyl vinyl ketone see reference [115].…”

Section: Morita-baylis-hillman Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

200

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

Cited by 98 publications

References 68 publications

Stereoselective synthesis of 3-amino-2-oxindoles from isatin imines: new scaffolds for bioactivity evaluation

Stereoselective synthesis of 3-amino-2-oxindoles from isatin imines: new scaffolds for bioactivity evaluation

Recent advances in the asymmetric catalytic synthesis of chiral 3-hydroxy and 3-aminooxindoles and derivatives: Medicinally relevant compounds

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

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