Enantioselective Silver-Catalyzed Transformations

Pellissier, Hélène

doi:10.1021/acs.chemrev.6b00639

Cited by 119 publications

(50 citation statements)

References 327 publications

(397 reference statements)

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“…Related 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 available by using various types of chiral silver complexes. The first example of asymmetric silver-catalyzed domino reaction was reported in 1990 by Ito et al, dealing with a domino aldol/cyclization reaction of aldehydes with tosylmethyl isocyanide promotted by chiral ferrocenylphosphine/silver complexes with high enantioselectivity (86% ee).…”

Section: Enantioselective Silver-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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Section: Enantioselective Silver-catalyzed Domino Reactionsmentioning

confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Pellissier

2019

Adv Synth Catal

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“…Rare earth metal chiral catalysts have been applied in the last two decades to promote asymmetric Michael reactions [58]. Among them, several chiral yttrium complexes recently provided remarkable results.…”

Section: Enantioselective Yttrium-catalyzed Michael Additionsmentioning

confidence: 99%

Recent developments in enantioselective yttrium-catalyzed transformations

Pellissier

2016

Coordination Chemistry Reviews

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“…The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol %) without impacting its efficiency.Since formulated by R. C. Fuson in 1935, [1] the concept of vinylogy which expands the character of an electrophilic or nucleophilic functional group to propagate to a remote point over a conjugated system, has widely been applied to the development of carbon-carbon bond formation methods. [2] Nowadays, it is still a versatile strategy for synthetic organic chemistry that attracts much attention from the viewpoint of atom economy as well as green chemistry. Among fruitful achievements, the catalytic asymmetric vinylogous Michael addition (VMA) serves as one of the most efficient tools to access optically active γ-functionalized α,β-unsaturated carbonyl compounds, [3] it is also a highly efficient pathway to obtain chiral building blocks and scaffolds in synthetic chemistry.…”

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Chiral‐at‐Metal Rhodium(III) Complex Catalyzed Enantioselective Vinylogous Michael Addition of α,α‐Dicyanoolefins with α,β‐Unsaturated 2‐Acyl Imidazoles

Lin

et al. 2019

ChemCatChem

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As a development of traditional vinylogous Michael addition reactions, catalytic enantioselective γ‐functionalization of α,α‐dicyanoolefins possesses a remarkable advantage in carboxylic derivatives synthesis and has emerged as a powerful tool for the preparation of high value chemicals. In another hand, the development of versatile and highly efficient catalyst is quite critical for such asymmetric transformations. Herein, a newly developed chiral‐at‐metal rhodium (III) complex catalyzed enantioselective vinylogous Michael addition of α,α‐dicyanoolefins with α,β‐unsaturated 2‐acyl imidazoles has been realized, delivering the corresponding adducts in 68−89 % yields with up to 95 % enantioselectivity. The reaction can be conducted on a gram‐scale using a low catalyst loading (0.5 mol %) without impacting its efficiency.

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Enantioselective Silver-Catalyzed Transformations

Abstract: This review collects the major progress in the field of enantioselective transformations promoted by chiral silver catalysts, covering the literature since 2008, well illustrating the power of these especially mild Lewis acid catalysts to provide novel asymmetric reactions.

Cited by 119 publications

References 327 publications

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Recent developments in enantioselective yttrium-catalyzed transformations

Chiral‐at‐Metal Rhodium(III) Complex Catalyzed Enantioselective Vinylogous Michael Addition of α,α‐Dicyanoolefins with α,β‐Unsaturated 2‐Acyl Imidazoles

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