Cation‐Triggered Switchable Asymmetric Catalysis with Chiral Aza‐CrownPhos

Ouyang, Guanghui; He, Yong; Li, Yong; Xiang, Junfeng; Fan, Qing‐Hua

doi:10.1002/anie.201411593

Cited by 92 publications

(45 citation statements)

References 62 publications

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“…In one case, the opposite enantioselectivity is obtained by using the same molecule while changing its conformation . In another case, the structure of chiral self‐assemblies can be easily tuned by changing temperature, solvent, and host–guest reactions, thus, the development of smarter supramolecular catalysts is expected in the future …”

Section: Discussionmentioning

confidence: 99%

Self‐Assembled Chiral Nanostructures as Scaffolds for Asymmetric Reactions

Jiang

Ouyang

Zhang

et al. 2017

Chemistry A European J

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The asymmetric reaction is one of the most important reactions in organic synthesis. While a large number of efficient molecular catalysts have been developed and applied, recently, supramolecular and nanostructured catalysts have been attracting interest. In this Minireview, we focus on self-assembled chiral nanostructures and review their possibility and feasibility as enantioselective catalysts. The design concept and the requirement of the chiral scaffold as the catalysts are discussed. Based on the chirality and catalytic performance of the building molecules and the supramolecular nanostructures, the nanocatalyst is divided into chiral nanostructure driven (CND) and chiral nanostructure enhanced (CNE) enantioselective catalysts. Then, several typical self-assembled chiral nanostructures such as nanocages, nanotubes, nanorods, micelles and vesicles are selected as the chiral scaffold and their catalytic behaviors for the asymmetric reactions were demonstrated. Finally, the future developments of the field are also discussed.

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Section: Discussionmentioning

confidence: 99%

Self‐Assembled Chiral Nanostructures as Scaffolds for Asymmetric Reactions

Jiang

Ouyang

Zhang

et al. 2017

Chemistry A European J

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“…A remarkable example of cation‐triggered switchable asymmetric catalysis was reported by Fan and co‐workers . The authors designed a phosphoramidite ligand 87 modified with an aza‐crown ether and employed it in rhodium‐catalyzed asymmetric hydrogenation of dehydroamino acid esters (Scheme ).…”

Section: Ion‐ and Neutral Molecule‐switchable Dynamic Catalystsmentioning

confidence: 99%

Dynamic Responsive Systems for Catalytic Function

Vlatković

Collins

Feringa

2016

Chemistry A European J

113

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Responsive systems have recently gained much interest in the scientific community in attempts to mimic dynamic functions in biological systems. One of the fascinating potential applications of responsive systems lies in catalysis. Inspired by nature, novel responsive catalytic systems have been built that show analogy with allosteric regulation of enzymes. The design of responsive catalytic systems allows control of catalytic activity and selectivity. In this Review, advances in the field over the last four decades are discussed and a comparison is made amongst the dynamic responsive systems based on the principles underlying their catalytic mechanisms. The catalyst systems are sorted according to the triggers used to achieve control of the catalytic activity and the distinct catalytic reactions illustrated.

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“…Fan and colleagues reported a BINOL‐based phosphoramidite ligand bearing an aza‐crown ether moiety. They were able to switch between catalytically active and inactive states by addition or removal of Na + ions that suppress rhodium coordination of the crown ether . The implementation of sulfonamides was shown to be successful in the design of self‐sorting binuclear catalysts by Reek and colleagues.…”

Section: Introductionmentioning

confidence: 99%

A stereodynamic phosphoramidite ligand derived from 3,3′‐functionalized ortho‐biphenol and its rhodium(I) complex

et al. 2016

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Stereodynamic ligands and complexes bearing functional groups to attach chiral or achiral binding sites and auxiliaries are highly attractive due to the interesting opportunities for controlling the stereochemical outcome of enantioselective transformations. In this study we report the preparation of a 3,3'-functionalized biphenol (BIPOL) phosphoramidite ligand (P ) bearing 3,5-dichlorobenzoyl (3,5-DCB) amide binding sites for noncovalent interactions. Upon coordination to [Rh(COD) ]BF this substitution pattern directs one of the 3,5-DCB binding sites in close proximity of the metal center resulting in liberation of both COD ligands and the formation of a [Rh(P ) ]BF complex. Coordination of the amide carbonyl unit was found to be reversible, since the complex acted as an active catalyst in the hydrogenation of dehydroamino acid derivatives. X-ray crystallographic investigation revealed that the second 3,5-DCB unit is capable of forming noncovalent π-π interactions connecting both phosphoramidite ligands.

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Cation‐Triggered Switchable Asymmetric Catalysis with Chiral Aza‐CrownPhos

Cited by 92 publications

References 62 publications

Self‐Assembled Chiral Nanostructures as Scaffolds for Asymmetric Reactions

Self‐Assembled Chiral Nanostructures as Scaffolds for Asymmetric Reactions

Dynamic Responsive Systems for Catalytic Function

A stereodynamic phosphoramidite ligand derived from 3,3′‐functionalized ortho‐biphenol and its rhodium(I) complex

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