Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation

Wu, Hua-Bin; Handoko,; Raj, Monika; Arora, Paramjit S.

doi:10.1021/acs.orglett.7b02412

Cited by 17 publications

(17 citation statements)

References 21 publications

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“…13 C{H} NMR (101 MHz, CDCl 3 ): δ 139.6, 137.5, 129.4, 127.7, 127.2, 125.8, 57.2, 46.5, 21.2, 11.4. Spectral data is in agreement with published data …”

Section: Methodssupporting

confidence: 91%

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A BEt₃-Base Catalyst for Amide Reduction with Silane

Yao

Fang

et al. 2019

J. Org. Chem.

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Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt 3 and base. The scope of these BEt 3 -base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si−H•••B activation mode wherein the hydride abstraction by BEt 3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.

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“…13 C{H} NMR (101 MHz, CDCl 3 ): δ 139.6, 137.5, 129.4, 127.7, 127.2, 125.8, 57.2, 46.5, 21.2, 11.4. Spectral data is in agreement with published data …”

Section: Methodssupporting

confidence: 91%

“…Spectral data is in agreement with published data. 22 4.5.9. N-Ethyl-N-(furan-2-ylmethyl)ethanamine (2j).…”

Section: Methodsmentioning

confidence: 99%

A BEt₃-Base Catalyst for Amide Reduction with Silane

Yao

Fang

et al. 2019

J. Org. Chem.

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“…Arora et al have developed urea derivatives that catalyze the formationo fa mide bonds by the condensation of thioesters and amines. [157] The catalytic activityi ss ignificantly improvedb yi ntroducing at hiophenolm oiety that enables the transthioesterification of thioesters,a sw ell as at ertiarya mine moiety that activates the nucleophilic attack of amines into the appropriate sites through stepwiseo ptimization of the catalyst structure. Arora et al developed the catalyst structure further,a nd realized direct condensation reactions between carboxylic acids and amines (Scheme 4).…”

Section: Catalytic Reactionsmentioning

confidence: 99%

Urea Derivatives as Functional Molecules: Supramolecular Capsules, Supramolecular Polymers, Supramolecular Gels, Artificial Hosts, and Catalysts

Yokoya

Kimura

Yamanaka

2021

Chemistry A European J

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Urea, which has both hydrogen bond acceptor and donor moieties, is an ideal structuref or as upramolecular synthon. Various supramolecules having ureido group(s) have been widelyd eveloped. This article summarizes recent developments of urea derivatives that exhibit various functions:i)supramolecular capsules that form discreteu reaurea intermolecular hydrogen bonds, ii)supramolecular polymers that form continuous urea-urea intermolecularh ydrogen bonds, iii)supramolecular gels that form continuous urea-urea intermolecular hydrogen bonds, iv) artificialh ost molecules based on the molecular recognition ability of the ureido group, and v) catalytic reactions developedb yu tilizing the molecular recognition ability of the ureido group.

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“…Additional inspiration can be found in very creative work from Arora et al that has resulted in redox-active multifunctional catalysts of peptide bond formation from N-protected α-amino acid substrates . This chemistry is compatible with conventional solid-phase synthesis and sets a standard toward which future foldamer catalysis efforts can strive.…”

Section: Recent Lessons From Conventional Peptidesmentioning

confidence: 99%

Foldamer Catalysis

Girvin

Gellman

2020

J. Am. Chem. Soc.

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The extraordinary rate accelerations and control of reactivity exhibited by enzymes have long inspired efforts to develop synthetic catalysts. Foldamers, which are oligomers with a strong tendency to adopt a specific conformation, represent unique platforms for efforts to harness principles of enzyme function for catalyst design. Well-defined helical structures that have been identified in several foldamer families can serve as scaffolds for the predictable spatial arrangement of functional groups. The chirality of these helices offers a basis for asymmetric catalysis. Thus, foldamer-based approaches to catalyst development represent an attractive alternative to well-developed strategies involving small molecules or conventional peptides.

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Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation

Cited by 17 publications

References 21 publications

A BEt₃-Base Catalyst for Amide Reduction with Silane

A BEt₃-Base Catalyst for Amide Reduction with Silane

Urea Derivatives as Functional Molecules: Supramolecular Capsules, Supramolecular Polymers, Supramolecular Gels, Artificial Hosts, and Catalysts

Foldamer Catalysis

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Iterative Design of a Biomimetic Catalyst for Amino Acid Thioester Condensation

Cited by 17 publications

References 21 publications

A BEt3-Base Catalyst for Amide Reduction with Silane

A BEt3-Base Catalyst for Amide Reduction with Silane

Urea Derivatives as Functional Molecules: Supramolecular Capsules, Supramolecular Polymers, Supramolecular Gels, Artificial Hosts, and Catalysts

Foldamer Catalysis

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A BEt₃-Base Catalyst for Amide Reduction with Silane

A BEt₃-Base Catalyst for Amide Reduction with Silane