Enantioselective γ‐Alkylation of α,β‐Unsaturated Aldehydes Using New Cinchona‐Based Primary Amine Catalyst

Huang, Yong-Shuang; Song, Shuang-Gui; Ren, Lei; Li, Yougui; Wu, Xiang

doi:10.1002/ejoc.201901219

Cited by 4 publications

(1 citation statement)

References 45 publications

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“…Both naturally occurring and modified cinchona alkaloids (quinine, quinidine, cinchonidine, cinchonine) are widely used in asymmetric synthesis. These alkaloids offer various important features such as numerous chiral centers, structural rigidity, multiple donors in the form of hydrogen bonds, and facile conversion into different functional groups including chiral quaternary ammonium salts [81][82][83][84][85][86][87][88][89][90]. Apart from this, they have various applications such as utilization in chiral ligands in the preparation of metal complexes, in NMR as chiral agents, resolving agents, chiral stationary phase in HPLC, electrolytic additives, and chiral solvating agents.…”

Section: Cinchona Alkaloidsmentioning

confidence: 99%

Regiodivergent Organocatalytic Reactions

et al. 2021

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Organocatalysts are abundantly used for various transformations, particularly to obtain highly enantio- and diastereomeric pure products by controlling the stereochemistry. These applications of organocatalysts have been the topic of several reviews. Organocatalysts have emerged as one of the very essential areas of research due to their mild reaction conditions, cost-effective nature, non-toxicity, and environmentally benign approach that obviates the need for transition metal catalysts and other toxic reagents. Various types of organocatalysts including amine catalysts, Brønsted acids, and Lewis bases such as N-heterocyclic carbene (NHC) catalysts, cinchona alkaloids, 4-dimethylaminopyridine (DMAP), and hydrogen bond-donating catalysts, have gained renewed interest because of their regioselectivity. In this review, we present recent advances in regiodivergent reactions that are governed by organocatalysts. Additionally, we briefly discuss the reaction pathways of achieving regiodivergent products by changes in conditions such as solvents, additives, or the temperature.

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Section: Cinchona Alkaloidsmentioning

confidence: 99%

Regiodivergent Organocatalytic Reactions

et al. 2021

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Synergistic Organo‐Organocatalysis

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Sinibaldi

et al. 2022

Asymmetric Organocatalysis

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Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

et al. 2021

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The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of aminoorganocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MS n showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.

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Enantioselective γ‐Alkylation of α,β‐Unsaturated Aldehydes Using New Cinchona‐Based Primary Amine Catalyst

Cited by 4 publications

References 45 publications

Regiodivergent Organocatalytic Reactions

Regiodivergent Organocatalytic Reactions

Synergistic Organo‐Organocatalysis

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

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