An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid‐Catalysed Pictet–Spengler Reactions of Isatins

Duce, Sara; Pesciaioli, Fabio; Gramigna, Lucia; Bernardi, Luca; Mazzanti, Andrea; Ricci, Alfredo; Bartoli, Giuseppe; Bencivenni, Giorgio

doi:10.1002/adsc.201100050

Cited by 152 publications

(55 citation statements)

References 72 publications

(15 reference statements)

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“…8c,13 We have previously shown that this reaction is efficiently catalyzed using Lewis acidic metal salts, thioureas, or BINOL-derived chiral phosphoric acids. The 5-fluorospiroindolone 16b was prepared using a BINOL-derived phosphoric acid catalyst to demonstrate the enantioselective synthesis and evaluate the retention of enantiomeric excess in the CuAAC reaction.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Stereoselective Synthesis of Diverse Oxindoles and Spirooxindoles from Isatins

et al. 2012

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A strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles is presented. Using a common set of N-propargylated isatins, a series of mechanistically-distinct stereoselective reactions with different combinations of nucleophiles and catalysts provide access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting N-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Overall, this strategy affords a 64-member pilot-scale library of diverse oxindoles and spirooxindoles.

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Section: Resultsmentioning

confidence: 99%

Catalytic Stereoselective Synthesis of Diverse Oxindoles and Spirooxindoles from Isatins

et al. 2012

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“…Noteworthy examples are Povarov reactions, O-alkylations, Pictet-Spengler reactions or benzidine rearrangement [73][74][75][76]. Chiral BA have shown particularly successful performances in the acetalisation reaction [77][78][79].…”

Section: Brønsted Acid Catalysismentioning

confidence: 99%

Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

Federsel¹

2014

ScienceOpen Research

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Organocatalysis, that is the use of small organic molecules to catalyse organic transformations, has been included among the most successful concepts in asymmetric catalysis and it has been used for the enantioselective construction of C-C, C-N, C-O, C-S, C-P, and C-halide bonds. Since the seminal works in early 2000, the scientific community has been paying an ever-growing attention to the use of organocatalysts for the synthesis, with high yields and remarkable stereoselectivities, of optically active fine chemicals of interest for the pharmaceutical industry. A brief overview is here presented about the two main classes of substrate activation by the catalyst: covalent organocatalysis and non-covalent organocatalysis, with a more stringent focus on some recent outcomes in the field of the latter and of hydrogen-bond-based catalysis. Finally, some successful examples of heterogenisation of organocatalysts are also discussed, in the view of a potential industrial exploitation.

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“…Molecules bearing a spirocyclic oxindole ring (spirooxindole) system are widely found in nature and have recently attracted significant attention because of their unique structure and broad biological activities such as antitumor , antitubercular , antimicrobial , antifungal , antimycobacterial , antimalarial , and antioxidant and can also serve as synthetic intermediates for alkaloids and many kinds of pharmaceuticals or drug precursors . Furthermore, organophosphorous heterocycles, especially an oxazaphosphorines structure, such as cyclophosphamide, ifosfamide (Fig.…”

Section: Introductionmentioning

confidence: 99%

Efficient One‐Pot Synthesis of Novel Spirooxindole‐Fused Phosphorous Heterocycle Derivatives by a Three‐Component Domino Reaction

Liu

2014

Heteroatom Chemistry

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A highly efficient, catalyst‐free, and regioselective synthesis of structurally diverse spirooxindole‐fused phosphorous heterocycle derivatives was constructed in good yields by means of a three‐component domino reaction of isatins, dichlorophenylphosphine or phenyl phosphorodichloridite, and o‐aminophenol in tetrahydrofuran reflux. The advantages of this method include high efficiency, mild reaction conditions, and environmentally benign reagents. These spirooxindole‐fused phosphorous heterocycles are promising candidates for drug discovery.

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An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid‐Catalysed Pictet–Spengler Reactions of Isatins

Cited by 152 publications

References 72 publications

Catalytic Stereoselective Synthesis of Diverse Oxindoles and Spirooxindoles from Isatins

Catalytic Stereoselective Synthesis of Diverse Oxindoles and Spirooxindoles from Isatins

Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

Efficient One‐Pot Synthesis of Novel Spirooxindole‐Fused Phosphorous Heterocycle Derivatives by a Three‐Component Domino Reaction

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