Asymmetric cross aldol addition of isatins with α,β-unsaturated ketones catalyzed by a bifunctional Brønsted acid–Brønsted base organocatalyst

Liu, Guo‐Gui; Zhao, Hua; Lan, Yu‐Bao; Wu, Bin; Huang, Xiaofei; Chen, Jian; Tao, Jing‐Chao; Wang, Xingwang

doi:10.1016/j.tet.2012.03.042

Cited by 45 publications

(13 citation statements)

References 59 publications

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“…24 The application of C9 amine derivative 10 in this reaction took much longer (10 hours) and offered relatively lower yields (up to 58%) and enantioselectivity (up to 90%). The mechanism proposed is similar to one proposed by Liu et al 23 The enolate is generated by abstraction of proton from ketones/aldehydes by quinuclidine nitrogen, and isatin is activated by H-bonding with urea moiety.…”

Section: Application Of C9 Urea/thiourea Derivativessupporting

confidence: 61%

“…22 Liu et al also employed Cinchona alkaloid-derived thioureas ( Figure 10) in asymmetric aldol reactions of isatins with α,β-unsaturated ketones affording aldol adducts at moderate-to-good yields (18%-98%) and with moderateto-high enantioselectivity (30%-97% EE). 23 The authors proposed that the enones were deprotonated by the tertiary amine of the quinuclidine and isatin activated and oriented by hydrogen bonding of its carbonyl group with a thiourea moiety in the catalyst.…”

Section: Application Of C9 Urea/thiourea Derivativesmentioning

confidence: 99%

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Recent applications of <em>Cinchona</em> alkaloid-based catalysts in asymmetric addition reactions

Singh¹,

Yeboah²

2016

ROC

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This review documents recently developed asymmetric addition reactions catalyzed by natural Cinchona alkaloids and their derivatives. These reactions include direct nucleophilic additions across the carbon-oxygen double bond and the carbon-nitrogen double bond, 1,4-additions, and cycloadditions. Natural and modified Cinchona alkaloids with different functionalities, such as amino, alkoxy, hydroxyl, amido, urea, and thiourea, especially on position C9, have been employed as catalysts in these reactions. Mechanistic considerations are discussed in many cases. In some cases, the application of adducts in further synthesis is also described.

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Section: Application Of C9 Urea/thiourea Derivativessupporting

confidence: 61%

Section: Application Of C9 Urea/thiourea Derivativesmentioning

confidence: 99%

Recent applications of <em>Cinchona</em> alkaloid-based catalysts in asymmetric addition reactions

Singh¹,

Yeboah²

2016

ROC

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“…The most direct approach to 3-substituted-3-hydroxy oxindoles is a nucleophilic addition of appropriate nucleophiles to isatins, such as the aldol reaction or an alkylation of isatins. Recently, several elegant approaches to 3-aryl or alkyl-3-hydroxyindolin-2-ones via the cross-aldol reaction between isatins and ketones have been extensively studied [22][23][24][25][26][27][28][29][30][31]. However, few examples of the corresponding aldol reactions of various α,β-unsaturated ketones with isatins were found in the literature.…”

Section: Figurementioning

confidence: 99%

Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins

et al. 2013

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An efficient approach for the synthesis of 3-substituted-3-hydroxy-2-oxindoles has been achieved via an aldol reaction of α,β-unsaturated ketones and isatins using arginine as an organocatalyst. A range of 3-substituted-3-hydroxy-2-oxindoles were obtained in moderate to high (up to 99%) yields. These 3-substituted-3-hydroxy-2-oxindoles with an additional enone moiety provide an opportunity for further elaboration of the products and for potentially interesting biological activities. In addition, the formation of 3-substituted-3-hydroxy-2-oxindole 3a was confirmed by X-ray crystallography. The possible reaction mechanism reveals that the reaction proceeds via a double action process.

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“…In another example, the same kind of reaction was explored, this time in the preparation of 3-(2Hchromen-2-one)-3-hydroxyoxindole derivatives, using isatin and 3-acetyl-2H-chromen-2-ones as starting materials and a quinidineurea bifunctional catalyst (C10 e Scheme 6 c)) [67]. Aldol adducts were also synthesized in moderate to good yields and enantioselectivities using isatin derivatives and a,b-unsaturated ketones as starting materials, in the presence of the quinidine-thiourea organocatalyst C8 and its epimer C11 (Scheme 6 d)) [68].…”

Section: Cinchona Alkaloidsmentioning

confidence: 99%

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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Asymmetric cross aldol addition of isatins with α,β-unsaturated ketones catalyzed by a bifunctional Brønsted acid–Brønsted base organocatalyst

Cited by 45 publications

References 59 publications

Recent applications of <em>Cinchona</em> alkaloid-based catalysts in asymmetric addition reactions

Recent applications of <em>Cinchona</em> alkaloid-based catalysts in asymmetric addition reactions

Facile Creation of 3-Substituted-3-Hydroxy-2-Oxindoles by Arginine-Catalyzed Aldol Reactions of α,β-Unsaturated Ketones with Isatins

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

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