Bifunctional Cinchona Alkaloid Catalyzed Vinylogous Michael Reaction of 3–Alkylideneoxindole with 4‐Oxo‐enoates: A Route to Chiral γ‐Keto Alkylideneoxindole Esters

Asymmetric vinylogous conjugate addition reactions constitute an essential class of enantioselective CÀ C bond-forming transformations characterized by remote functionalization of substrates and the construction of distal stereocenters. After the renaissance of organocatalysis in 2000, vinylogous addition methodologies have seen new horizons of development. Cinchona alkaloids and some of their derivatives have appeared as efficient chiral catalysts in several organic transformations. Their non-toxicity, low cost, availability in pseudo-enantiomeric forms, and "open flask" reaction procedures have been the main reasons behind their success in asymmetric synthesis. These organocatalysts have also shown remarkable applications in vinylogous chemistry. This mini-review covers the developments of asymmetric vinylogous conjugate addition (VCA) reactions under bifunctional cinchona alkaloids/derivatives catalysis.

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Cinchona Derivatives as Bifunctional H‐bonding Organocatalysts in Asymmetric Vinylogous Conjugate Addition Reactions

Joshi

Singh

2022

Asian J Org Chem

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DBU‐Catalyzed Regioselective α‐Alkylation of Enones Using the Vinylogous Strategy

Tian

Shang

2021

Asian J Org Chem

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A convenient and atom-economic transformation of enones with electron-deficient alkenes under mild conditions has been developed using DBU as a catalyst. This method utilizes vinylogous strategy to form dienolate intermediates, which provides a new approach for the regioselective α-alkylation of enones. This protocol exhibits a broad range of substrate scope and good functional group compatibility. Moreover, it enabled the formation of unexpected cyclic 1,5-diketone by employing phenyl acrylate as Michael acceptor to construct all-carbon quaternary centers at γ-position of enones. Overall, this synthetic method establishes a new route from readily available enones to valuable 1,5-dicarbonyl compounds.

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Exploitation of Dimeric Cyclic Cysteine as Helix Inducer in Ultra‐Short Peptides for Cu(II)‐Catalyzed Asymmetric Michael Addition on Chalcones

et al. 2023

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Dedicated to Prof. Cesare Gennari on the occasion of his 70 th birthday.A dimeric cyclic cysteine analogue, i.e. (1R,1'R,2R,2'R)-2,2'disulfanediylbis (aminocyclohexane-1-carboxylic acid), was used as a constrained unnatural amino acid and as a folding inducer in ultra-short Leu-Val-containing peptide. Our results showed that both free dimer amino acid L1 and its peptide derivative L2 are able to chelate Cu(II). The obtained complexes resulted to be catalytically active in Michael addition reaction of nitromethane on different types of chalcones. L1-Cu(II) was shown more reactive in terms of conversion, while, in neat conditions, L2-Cu(II) allows to obtain an interesting 60 % e.e. on pyridine chalcone.

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Bifunctional Cinchona Alkaloid Catalyzed Vinylogous Michael Reaction of 3–Alkylideneoxindole with 4‐Oxo‐enoates: A Route to Chiral γ‐Keto Alkylideneoxindole Esters

Cited by 4 publications

References 68 publications

Cinchona Derivatives as Bifunctional H‐bonding Organocatalysts in Asymmetric Vinylogous Conjugate Addition Reactions

Cinchona Derivatives as Bifunctional H‐bonding Organocatalysts in Asymmetric Vinylogous Conjugate Addition Reactions

DBU‐Catalyzed Regioselective α‐Alkylation of Enones Using the Vinylogous Strategy

Exploitation of Dimeric Cyclic Cysteine as Helix Inducer in Ultra‐Short Peptides for Cu(II)‐Catalyzed Asymmetric Michael Addition on Chalcones

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