Construction of 3-amino-2-oxindoles by direct amination of aniline or α-amino-acid derivatives to 3-bromooxindoles

Zhao, Min; Li, Nai‐Kai; Zhang, Yafei; Pan, Feng‐Feng; Wang, Xingwang

doi:10.1016/j.tet.2016.01.039

Cited by 13 publications

(6 citation statements)

References 102 publications

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“…Using indolines as the nucleophiles and chiral Box‐Ni II complex catalyst, the Wang group realized asymmetric synthesis of N ‐tryptamine‐related 3‐alkyloxindole, a precursor for the total synthesis of (+)‐psychotrimine [12] . However, the amination of 3‐bromo‐3‐benzyl oxindole with anilines rendered the desired products with high yield but moderate enantioselectivity, [13] which might be due to the background reaction and amine‐poisoning of the metal catalysts.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

Wen-kun

Dong

et al. 2021

Chemistry A European J

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A chiral N,N'-dioxide-nickel(II) complex-catalyzed asymmetric amination of 3-bromo-3-substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3amino-indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3-amino-2oxindole-based bioactive compounds. Moreover, a possible transition-state model is proposed so as to elucidate the origin of the chirality based on the X-ray crystal structure of the catalyst and the adduct.

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Section: Methodsmentioning

confidence: 99%

Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

Wen-kun

Dong

et al. 2021

Chemistry A European J

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“…This method was applied to the formal synthesis of the cytotoxic alkaloid (+)-psychotrimine, which exhibits potent antitumor activity against colon and lung cancers 290 and antibacterial activity against Grampositive bacteria. 291 The same group 292 reported the enantioconvergent amination of 3-bromooxindoles 262 with anilines under Ni(dppp)Cl 2 /bis(oxazoline) 211 catalysis to give 3-anilinooxindoles 439 with good yields and moderate enantioselectivities (Scheme 135a). In the proposed mechanism, the racemic 3bromooxindole undergoes a base-mediated dehydrohalogenative process to provide ortho-azaxylylene I.…”

Section: Amination Of 3-bromooxindolesmentioning

confidence: 99%

Metal-Catalyzed Enantioconvergent Transformations

Yus,

Nájera,

Foubelo

et al. 2023

Chem. Rev.

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Enantioconvergent catalysis has expanded asymmetric synthesis to new methodologies able to convert racemic compounds into a single enantiomer. This review covers recent advances in transition-metal-catalyzed transformations, such as radical-based cross-coupling of racemic alkyl electrophiles with nucleophiles or racemic alkylmetals with electrophiles and reductive cross-coupling of two electrophiles mainly under Ni/bis(oxazoline) catalysis. C–H functionalization of racemic electrophiles or nucleophiles can be performed in an enantioconvergent manner. Hydroalkylation of alkenes, allenes, and acetylenes is an alternative to cross-coupling reactions. Hydrogen autotransfer has been applied to amination of racemic alcohols and C–C bond forming reactions (Guerbet reaction). Other metal-catalyzed reactions involve addition of racemic allylic systems to carbonyl compounds, propargylation of alcohols and phenols, amination of racemic 3-bromooxindoles, allenylation of carbonyl compounds with racemic allenolates or propargyl bromides, and hydroxylation of racemic 1,3-dicarbonyl compounds.

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“…Recently, the synthesis of chiral 3-amino-3-substituted oxindoles was reported through the application of a chiral catalyst complex Ni(dppp)Cl 2 /bis(oxazoline) ligand L25. In this study, the substrates consisted of 3-bromo-3-substituted-oxindole derivatives and anilines, and the final products were obtained in good yields and enantioselectivity (Scheme 74) [214].…”

Section: Period 4 E Sc Fe Nimentioning

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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Construction of 3-amino-2-oxindoles by direct amination of aniline or α-amino-acid derivatives to 3-bromooxindoles

Cited by 13 publications

References 102 publications

Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

Metal-Catalyzed Enantioconvergent Transformations

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

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