Enantioselective Gold-Catalyzed Pictet–Spengler Reaction

Glinsky-Olivier, Nicolas; Yang, Shengwen; Retailleau, Pascal; Gandon, Vincent; Guinchard, Xavier

doi:10.1021/acs.orglett.9b03656

Cited by 55 publications

(26 citation statements)

References 61 publications

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“…Recently, in 2019, Guinchard and co‐workers [15] disclosed an enantioselective gold‐catalyzed Pictet‐Spengler reaction (Scheme 10). The Pictet‐Spengler reaction is an acid‐catalyzed condensation between β‐arylethylamines and aldehydes affording tetrahydroisoquinolines or tetrahydro‐β‐carbolines, through iminium intermediates.…”

Section: Recent Development Of Enantioselective Gold(i) Catalysismentioning

confidence: 99%

Recent Advances in the Development of Chiral Gold Complexes for Catalytic Asymmetric Catalysis

Jiang

Wong

2021

Chemistry An Asian Journal

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Asymmetric gold catalysis has been rapidly developed in the past ten years. Breakthroughs have been made by rational design and meticulous selection of chiral ligands. This review summarizes newly developed gold‐catalyzed enantioselective organic transformations and recent progress in ligand design (since 2016), organized according to different types of chiral ligands, including bisphosphine ligands, monophosphine ligands, phosphite‐derived ligands, and N‐heterocyclic carbene ligands for asymmetric gold(I) catalysis as well as heterocyclic carbene ligands and oxazoline ligands for asymmetric gold(III) catalysis.

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Section: Recent Development Of Enantioselective Gold(i) Catalysismentioning

confidence: 99%

Recent Advances in the Development of Chiral Gold Complexes for Catalytic Asymmetric Catalysis

Jiang

Wong

2021

Chemistry An Asian Journal

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“…2) [31]. Finally, along with this alkyne activation protocols, (R)-DTBM-SEGPHOS(AuCl) 2 has been efficiently applied in asymmetric Picted-Spengler reactions between tryptamines and arylaldehydes [32].…”

Section: Gold(i) Asymmetric Transformations 21 Gold(i) Asymmetric Transformations With Diphosphine Ligandsmentioning

confidence: 99%

Gold Catalyzed Asymmetric Transformations

García¹

2021

Current Topics in Chirality - From Chemistry to Biology

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In this chapter, the strategies developed to attain asymmetric reactions with gold are disclosed. Because of its preferred linear arrangement, to induce asymmetry, gold(I) needs to fulfill one of the following requirements: a) the use of bulky chiral ligands, that create a chiral pocket around the active site, b) the coordination to bifunctional ligands capable to establish secondary interactions with substrates, or c) tight ion pairing with chiral counteranions. On the other hand, gold(III) profits of a square-planar coordination mode, which approaches chiral ligands to substrates. However, its tendency to be reduced leads to difficulties for its applications in catalytic asymmetric transformations. Pioneering works using cyclometaled structures, have found the balance between stability and activity, showing its potential in asymmetric transformations.

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“…Lastly, the model predicts that an enzymatic Pictet-Spengler reaction catalyzed by EC 4.2.1.x, can convert dopamine and the corresponding aldehyde to the alkaloid (S )-norlaudanosoline (5) enantioselectively, which typically requires the presence of organocatalysts or transition metals. [33][34][35] It is interesting to compare the routes suggested by our model with the ones from RetroBioCat. 18 In reaction ( 1) the starting substrate is styrene, which undergoes epoxidation in presence of an epoxidase, followed by epoxide opening, partial oxidation of the primary alcohol to aldehyde and transamination.…”

Section: Retrosynthesis Use-casesmentioning

confidence: 99%

Molecular Transformer-aided Biocatalysed Synthesis Planning

Probst¹,

Manica²,

Teukam³

et al. 2021

Preprint

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Enzyme catalysts are an integral part of green chemistry strategies towards a more sustainable and resource-efficient chemical synthesis. However, the use of enzymes on unreported substrates and their specific stereo- and regioselectivity are domain-specific knowledge factors that require decades of field experience to master. This makes the retrosynthesis of given targets with biocatalysed reactions a significant challenge. Here, we use the molecular transformer architecture to capture the latent knowledge about enzymatic activity from a large data set of publicly available biochemical reactions, extending forward reaction and retrosynthetic pathway prediction to the domain of biocatalysis. We introduce the use of a class token based on the EC classification scheme that allows to capture catalysis patterns among different enzymes belonging to the same hierarchical families. The forward prediction model achieves an accuracy of 49.6% and 62.7%, top-1 and top-5 respectively, while the single-step retrosynthetic model shows a round-trip accuracy of 39.6% and 42.6%, top-1 and top-10 respectively. Trained models and curated data are made publicly available with the hope of promoting enzymatic catalysis and making green chemistry more accessible through the use of digital technologies.

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Enantioselective Gold-Catalyzed Pictet–Spengler Reaction

Cited by 55 publications

References 61 publications

Recent Advances in the Development of Chiral Gold Complexes for Catalytic Asymmetric Catalysis

Recent Advances in the Development of Chiral Gold Complexes for Catalytic Asymmetric Catalysis

Gold Catalyzed Asymmetric Transformations

Molecular Transformer-aided Biocatalysed Synthesis Planning

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