Asymmetric Organocatalysis—A Powerful Technology Platform for Academia and Industry: Pregabalin as a Case Study

Giorgianni, Giuliana; Bernardi, Luca; Fini, Francesco; Pesciaioli, Fabio; Secci, Francesco; Carlone, Armando

doi:10.3390/catal12080912

Cited by 2 publications

(2 citation statements)

References 71 publications

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“…These compounds can be easily converted into amines by reduction, which is used in known procedures. [20] In each case, the enantiomeric excess remained untouched, as demonstrated by HPLC measurements. This clearly shows that the proposed sequence of reactions from pyruvic acid ester to GABA precursors can be implemented in a very simple and effective way.…”

Section: Resultsmentioning

confidence: 88%

“…To prove the effectiveness and versatility of the method, we also obtained precursors of Baclofen ( 6 h from ( S )‐3 h , 64%) and Pregabalin ( 6 w from 3 w , 55%). These compounds can be easily converted into amines by reduction, which is used in known procedures [20] . In each case, the enantiomeric excess remained untouched, as demonstrated by HPLC measurements.…”

Section: Resultsmentioning

confidence: 99%

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Organocatalytic Activation of Pyruvates Toward Michael Addition to Nitroalkenes: Synthesis of γ‐Aminobutyric Acid (GABA) Derivatives

Włoszczak,

Karczewski,

Mlynarski

2024

Adv Synth Catal

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Despite the significant role of pyruvic acid in biotransformations, the utilization of pyruvates in the field of catalytic asymmetric synthesis has been unexpectedly limited. This statement also applies to enamine catalysis, in which pyruvates seem to be challenging substrates. Recently, the first illustration of the asymmetric addition of pyruvic acid to β‐nitrostyrenes, catalyzed by a NahE enzyme using the enamine mechanism, has appeared in the literature. Now, we demonstrate pyrrolidine‐based catalyst can mimick enamine mechanism used by this enzyme to activate pyruvates in the asymmetric addition to structurally diverse nitroalkenes to produce highly enantioenriched Michael adducts without the limitations in substrate structures associated with biocatalysts. In addition to confirming that optically pure pyrrolidines can serve as ultimately small organic catalysts in pyruvate activation, we present an exceedingly simple and versatile method for the synthesis of optically pure γ‐nitro acids, which are precursors for well‐known active pharmaceutical ingredients namely GABA derivatives

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Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Organocatalytic Activation of Pyruvates Toward Michael Addition to Nitroalkenes: Synthesis of γ‐Aminobutyric Acid (GABA) Derivatives

Włoszczak,

Karczewski,

Mlynarski

2024

Adv Synth Catal

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Nitrogen-Rich Carbon Dots as Effective Catalysts in the 1,4-Reduction of α,β-Unsaturated Aldehydes via Ion Pair Asymmetric Nano-Organocatalysis

Carioscia,

Cocco,

Casacchia

et al. 2024

ACS Catal.

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The development of nanostructured organocatalysts is emerging as a prominent field in materials science. To this purpose, nitrogen-doped carbon dots (CDs) have been effectively employed in enantioselective enamine organocatalysis. On the other hand, enantioselective iminium ion nano-organocatalysis is much less explored. In this Letter, the use of CDs in asymmetric iminium ion catalysis via asymmetric counteranion-directed catalysis (ACDC) is disclosed. Nonchiral CDs bearing butylenediamine residues proved to be the most effective ones, in combination with (S)-TRIP as a chiral phosphoric acid (CPA). A correlation between the features of the CDs' surfaces and their catalytic performance was shown, and the catalytic activity of the employed CDs proved to be higher than that of simple molecular amines. An extensive reaction optimization allowed the reduction of different α,β-unsatured aldehydes in good yield and ee, using a low catalyst loading.

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Asymmetric Organocatalysis—A Powerful Technology Platform for Academia and Industry: Pregabalin as a Case Study

Cited by 2 publications

References 71 publications

Organocatalytic Activation of Pyruvates Toward Michael Addition to Nitroalkenes: Synthesis of γ‐Aminobutyric Acid (GABA) Derivatives

Organocatalytic Activation of Pyruvates Toward Michael Addition to Nitroalkenes: Synthesis of γ‐Aminobutyric Acid (GABA) Derivatives

Nitrogen-Rich Carbon Dots as Effective Catalysts in the 1,4-Reduction of α,β-Unsaturated Aldehydes via Ion Pair Asymmetric Nano-Organocatalysis

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