Domino Reactions Initiated by Enantioselective Cu‐Catalyzed Conjugate Addition

Galeštoková, Zuzana; Šebesta, Radovan

doi:10.1002/ejoc.201200875

Cited by 58 publications

(16 citation statements)

References 81 publications

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“…Especially in the current case, subsequent reaction with a carbon electrophile is attractive, as a second, quaternary, stereocentre is formed. Reaction of in situ formed enolates has been reported a number of times,20,30–33 however, unlike lithium enolates, magnesium enolates react only sluggishly and additives or co‐solvents are mostly used to accelerate the reaction.…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalysed Conjugate Addition of Grignard Reagents to 2‐Methylcyclopentenone and Sequential Enolate Alkylation

et al. 2014

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The copper/Rev-JosiPhos-catalysed asymmetric conjugate addition of Grignard reagents to 2methylcyclopentenone (1) provides 2,3-disubstituted cyclopentanones in high yields and enantioselectivities, and good diastereoselectivities. Reaction of the in situ formed enolate with various alkylating reagents in the presence of 1,3-dimethyltetrahydropyrimidine-2(1H)-one (DMPU) affords the correspond-ing products in a one-pot reaction. This procedure creates two vicinal stereocentres, one of them quaternary.

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Section: Resultsmentioning

confidence: 99%

Copper‐Catalysed Conjugate Addition of Grignard Reagents to 2‐Methylcyclopentenone and Sequential Enolate Alkylation

et al. 2014

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“…Chiral copper catalysts have also been recently employed to promote asymmetric domino reactions. [46] For example in 2016, 10 mol% of CuI was combined with 20 mol% of a chiral proline-derived organocatalyst 58b to cooperatively catalyze enantioselective domino reactions between terminal alkynes 75/124 with 1-formyl-9H-E-carbolines 132. [47] This efficient multicatalysis opened a novel route for achieving biologically interesting chiral 5,6-dihydrocanthin-4-ones 133 in both moderate to high yields (57-92%) and enantioselectivities (68->99% ee), as shown in Scheme 33.…”

Section: Enantioselective Copper-catalyzed Domino Reactionsmentioning

confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Pellissier

2019

Adv Synth Catal

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This review collects the very recent developments in enantioselective metal-catalyzed domino reactions published since the beginning of 2016. It illustrates that many types of enantioselective metal-catalyzed domino processes continue to be developed, allowing an easy one-pot access to complex molecular architectures from simple starting materials taking economic advantages, such as avoiding costly protecting groups and timeconsuming purification procedures after each step. 1 Introduction 2 Enantioselective Silver-Catalyzed Domino Reactions 3 Enantioselective Scandium-and Yttrium-Catalyzed Domino Reactions 4 Enantioselective Iron-Catalyzed Domino Reactions 5 Enantioselective Cobalt-Catalyzed Domino Reactions 6 Enantioselective Magnesium-Catalyzed Domino Reactions 7 Enantioselective Zirconium-Catalyzed Domino Reactions 8 Enantioselective Rhodium-Catalyzed Domino Reactions 9 Enantioselective Palladium-Catalyzed Domino Reactions 10 Enantioselective Copper-Catalyzed Domino Reactions 11 Enantioselective Domino Reactions Catalyzed with Other Metals 12 Conclusions IntroductionAsymmetric metal catalysis constitutes a powerful tool to highly enantioselectively perform many types of reactions. [1] In particular, the combination of asymmetric metal catalysis with the concept of domino reactions has allowed high molecular complexity to be easily achieved with remarkable levels of stereocontrol on the basis of simple economic one-pot procedures. In the last decade, many types of enantioselective domino processes, including multicomponent ones, [2] have been successfully catalyzed by a wide variety of chiral metal complexes. [3] Introduced by Tietze, the concept of domino reactions consists in one-step two or more bond-forming transformations occurring under the same reaction conditions. [4] A range of complex densely functionalized chiral molecules, including natural and/or biologically important products, have already been synthesized through these processes without requiring the purification of intermediates. [5] The goal of this review is to collect the very recent advances in enantioselective metal-catalyzed domino reactions published since the beginning of 2016 since this field was most recently updated this year, covering the literature until the end of 2015 (including only 2 references from 2016). [6] It is divided into ten parts, dealing successively with enantioselective silver-catalyzed domino reactions, scandium-and yttrium-catalyzed domino reactions, iron-catalyzed domino reactions, cobalt-catalyzed domino reactions, magnesium-catalyzed domino reactions, zirconium-catalyzed domino reactions, rhodium-catalyzed domino reactions, palladium-catalyzed domino reactions, copper-catalyzed domino reactions and enantioselective domino reactions catalyzed by other metals. Enantioselective Silver-Catalyzed Domino ReactionsRelated to its moderate Lewis acidity, silver has long been neglected in catalysis. However, many highly efficient transformations, [7] including enantioselective domino reactions, [8] are today availabl...

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“…A number of domino reactions have been initiated by enantioselective copper-catalyzed Michael additions [4]. As an example in 2007, Alexakis and Li reported asymmetric copper-catalyzed domino double Michael reactions between dialkylzinc reagents 1 and bis-α,β-unsaturated carbonyl compounds 2 performed in the presence of chiral phosphoramidite ligands 3 and 4 [5].…”

Section: Michael-inititated Domino Reactionsmentioning

confidence: 99%

Green Copper Catalysis in Enantioselective Domino Reactions

Pellissier

2019

COC

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This review collects for the first time enantioselective domino reactions promoted by chiral green copper catalysts, covering the literature since the beginning of 2006. It is divided into two parts dealing successively with asymmetric twocomponent domino reactions and three-component processes. The first part is dedicated to two-component asymmetric domino reactions, including Michael-initiated processes, domino reactions based on cyclizations, domino reactions initiated by aldol-type condensations and Friedel−Crafts-initiated domino processes. The second part collects asymmetric threecomponent processes, such as Michael-initiated domino reactions, domino reactions between alkynes, aldehydes and amines, domino reactions based on 1,3-dipolar cycloadditions among other three-component reactions.

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Domino Reactions Initiated by Enantioselective Cu‐Catalyzed Conjugate Addition

Cited by 58 publications

References 81 publications

Copper‐Catalysed Conjugate Addition of Grignard Reagents to 2‐Methylcyclopentenone and Sequential Enolate Alkylation

Copper‐Catalysed Conjugate Addition of Grignard Reagents to 2‐Methylcyclopentenone and Sequential Enolate Alkylation

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Green Copper Catalysis in Enantioselective Domino Reactions

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