Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction

Martins, Rafaela de Souza; Pereira, Mathias Prado; Castro, Pedro P. de; Bombonato, Fernanda I.

doi:10.1016/j.tet.2019.130855

Cited by 14 publications

(7 citation statements)

References 28 publications

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“…N -(Boc)- l -phenylalanine p -nitroanilide ( 3 ): 1 H NMR (400 MHz, CDCl 3 ) δ = 8.50 (brs, 1H, -N H CO 2 ), 8.18 (d, J = 9.2 Hz, 2H, Ar- H ), 7.57 (d, J = 9.2 Hz, 2H, Ar- H ), 7.24–7.35 (m, 5H, -C 6 H 5 ), 5.04 (brs, 1H, -N H C(O)-), 4.46–4.50 (m, 1H, -NHC H (Bn)C(O)), 3.12–3.22 (m, 2H, Ph-C H 2 -), 1.44 (s, 9H, -C(C H 3 ) 3 ) ppm. [ 20 ]…”

Section: Methodsmentioning

confidence: 99%

A Molecular Probe with Both Chromogenic and Fluorescent Units for Detecting Serine Proteases

et al. 2021

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A molecular probe with l-phenylalanine p-nitroanilide and l-lysin 4-methylcoumaryl-7-amide, in which these amino acid derivatives are connected through a succinic-acid spacer, was prepared. Trypsin and papain were detected by blue-fluorescence emission of generated 7-amino-4-methylcoumarin (AMC). α-Chymotrypsin and nattokinase were detected from both the blue-fluorescence emission of AMC and the UV absorbance of p-nitroaniline. In addition, different time courses of p-nitroaniline and AMC were observed between the reaction of P1 with α-chymotrypsin and that with nattokinase. In the case of nattokinase, both the fluorescence emission and UV absorbance slowly increased. In contrast, the increasing UV absorbance was saturated at the early stage of the reaction of the present probe with chymotrypsin, whereas the fluorescence emission continuously increased in the following stages.

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Section: Methodsmentioning

confidence: 99%

A Molecular Probe with Both Chromogenic and Fluorescent Units for Detecting Serine Proteases

et al. 2021

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“…[α] D 25 +4.4 (c 5.0, CHCl 3 ); IR (CHCl 3 ) 3478,2957,2927,2852,1462,1366,1245,1188,1080,1037,970,931,894,758,722,666,606 7, 119.3, 109.1, 82.6, 79.5, 60.6, 33.6, 27.2, 26.9 (2S,3R,4R,5S)-1,2,5, . 16 The titled compound was prepared following the literature procedure from D-mannitol 12 (3.0 g, 16.468 mmol) to give 20 (3.93 g, 91%) as a white solid; mp 120−121 °C (120−122 °C). 16 [α] D 25 +6.5 (c 1.0, CHCl 3 ); IR (CHCl 3 ) ν max = 3446, 2991, 2934, 2881, 1457, 1383, 1373, 1253, 1156, 1069, 983, 942, 919, 856, 797, 516 cm −1 ; 1 H NMR (400 MHz, CDCl 3 ) δ = 4.09−4.01 (m, 4H), 3.94− 3.91 (m, 2H), 3.65 (t, J = 6.1 Hz, 2H), 3.28−3.24 (m, 2H), 1.33 (s, 6H), 1.28 (s, 6H) ppm; 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ = 109.2, 75.…”

Section: ■ Conclusionmentioning

confidence: 99%

Chiral Pool Meets Chiral Catalysis: Eight-Step Convergent Total Synthesis of Anticancer Natural Lipid Mycalol

Fernandes,

Choudhary,

Khatun

2023

J. Org. Chem.

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“…Bombonato et al ., [23] reported prolinamide catalysts ( 13 ) substituted with glycerol for accelerating asymmetric aldol reaction (Figure 3). Bulkier aldehydes and substituted cyclohexanones were well‐tolerated by the catalyst.…”

Section: Proline‐derived Amide Catalystsmentioning

confidence: 99%

Stereoselective Aldol and Conjugate Addition Reactions Mediated by Proline‐Based Catalysts and Its Analogues: A Concise Review

2021

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The application of amino acids and small peptides as asymmetric organocatalysts in the aldol and conjugate addition reactions is a significant breakthrough in the past decade. The desired stereoselectivity in these reactions can be attained through tunable elements of diversity present in the amino acids/peptides. On this note, the current review highlights the organocatalytic aldol and conjugate addition by proline or its analogous in the form of amide/peptide derivatives. The wide‐ranging works of literature are classified based on the use of single amino acid or peptides as a catalyst. The designing of the aforementioned amide/amino acid/peptide catalyst, including their recent applications, is also detailed. Moreover, the analogous catalysts are also discussed, embedding other hetero‐organic functionalities that mimic the catalytic activity of proline in aldol/conjugate additions.

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Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction

Cited by 14 publications

References 28 publications

A Molecular Probe with Both Chromogenic and Fluorescent Units for Detecting Serine Proteases

A Molecular Probe with Both Chromogenic and Fluorescent Units for Detecting Serine Proteases

Chiral Pool Meets Chiral Catalysis: Eight-Step Convergent Total Synthesis of Anticancer Natural Lipid Mycalol

Stereoselective Aldol and Conjugate Addition Reactions Mediated by Proline‐Based Catalysts and Its Analogues: A Concise Review

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