Assembly of chiral monodentate ligands to chelates by donor–acceptor interactions

Chuzel, Olivier; Magnier-Bouvier, Caroline; Schulz, Emmanuelle

doi:10.1016/j.tetasy.2008.04.008

Cited by 23 publications

(11 citation statements)

References 41 publications

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“…Activated silica modified by covalently grafted trinitrofluorenone was synthesized as a new material able to form supported CTC with ligand 1c (Scheme ). 2,5,7‐Trinitro‐9‐oxo‐9 H ‐fluorene‐4‐carboxylic acid 8 was synthesized in two steps from diphenic acid 32. By coupling with a trimethoxysilane functionalized propylamine in the presence of DCC, the trimethoxysilyl derivative 9 was obtained33 and directly grafted on activated silica as a suspension in refluxing toluene34 to yield the modified silica support 10 with a 0.191 mmol g −1 loading, as determined by elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

Charge‐Transfer Interactions: An Efficient Tool for Recycling Bis(oxazoline)‐Copper Complexes in Asymmetric Henry Reactions

Didier¹,

Magnier-Bouvier²,

Schulz³

2011

Adv Synth Catal

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An anthracenyl-modified chiral bis(oxazoline) copper complex has been demonstrated to efficiently promote nitroaldol reactions between structurally varying aldehydes and nitromethane or nitroethane. The catalyst was recovered through formation of a charge transfer complex between the chiral ligand and trinitrofluorenone and its subsequent precipitation with pentane. The efficiency of this procedure was proved through several consecutive catalytic cycles that allowed the sturdy formation of the expected product with a high enantioselectivity. The catalyst's stability was also put to the test in an original multi-substrate procedure. Following the same recovery concept, a new heterogeneous procedure was tested for which trinitrofluorenone was covalently linked to a silica support. Asymmetric heterogeneous catalysis was performed under these conditions as one of the few examples demonstrating the potential catalyst recycling in nitroaldol reactions through reversible, non-covalent interactions.

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Section: Resultsmentioning

confidence: 99%

Charge‐Transfer Interactions: An Efficient Tool for Recycling Bis(oxazoline)‐Copper Complexes in Asymmetric Henry Reactions

Didier¹,

Magnier-Bouvier²,

Schulz³

2011

Adv Synth Catal

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“…The development of libraries of new chiral transition‐metal complexes from combinations of known chiral and achiral ligands is expected to introduce a large diversity of catalytic properties for tackling issues of activity and selectivity raised by modern homogeneous catalysis. Considering the prominent role played by bidentate chiral phosphine ligands in late transition‐metal asymmetric catalysis, most combinatorial approaches to the design of ligating architectures have dealt with associations of two monodentate ligands (a phosphine or an N ‐heterocyclic carbene), the spatial arrangement of which around the metal center is dictated by steric repulsion20 or supramolecular interactions,21 including metal coordination,22 hydrogen bonding,23 and charge‐transfer complexation 24…”

Section: Introductionmentioning

confidence: 99%

Multiformat T‐Cell‐Engaging Bispecific Antibodies Targeting Human Breast Cancers

et al. 2015

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Four different formats of bispecific antibodies (bsAbs) were generated that consist of anti‐Her2 IgG or Fab site‐specifically conjugated to anti‐CD3 Fab using the genetically encoded noncanonical amino acid. These bsAbs varied in valency or in the presence or absence of an Fc domain. Different valencies did not significantly affect antitumor efficacy, whereas the presence of an Fc domain enhanced cytotoxic activity, but triggered antigen‐independent T‐cell activation. We show that the bsAbs can efficiently redirect T cells to kill all Her2 expressing cancer cells, including Her2 1+ cancers, both in vitro and in rodent xenograft models. This work increases our understanding of the structural features that affect bsAb activity, and underscores the potential of bsAbs as a promising therapeutic option for breast cancer patients with low or heterogeneous Her2 expression.

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“…Tolerating a large range of solvents, this type of interaction has its place in the recently described non‐covalent interactions to form supramolecular catalysts. Monophosphite or monooxazoline derivatives functionalized by electro‐donor and electro‐acceptor moieties have thus been assembled to promote enantioselective hydrogenations, by generating bidentate rhodium complexes, or Diels‐Alder reactions with copper species. More recently, Liang, Liu et al .…”

Section: Association Of Salen Complexes With Additives For Cooperativitymentioning

confidence: 99%

“…[88] Tolerating a large range of solvents, this type of interaction has its place in the recently described non-covalent interactions to form catalysts. Monophosphite [89] or monooxazoline [90] derivatives functionalized by electro-donor and electro-acceptor moieties have thus been assembled to promote enantioselective hydrogenations, by generating bidentate rhodium complexes, or Diels-Alder reactions with copper species. More recently, Liang, Liu et al synthesized three generations of Co-salen complexes containing electron deficient aromatic moieties, and studied the enhancement of cooperativity obtained after adding a proper electron rich compound.…”

Section: Association Of Salen Complexes With Additives For Cooperativitymentioning

confidence: 99%

Chiral Salen Complexes for Asymmetric Heterogeneous Catalysis: Recent Examples for Recycling and Cooperativity

2019

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Chiral salen complexes are privileged and versatile catalysts used in a wide variety of enantioselective transformations. Researches for their use in multicatalysis, including cooperative as well as tandem processes, are more recent, but many reports already highlight the important effect of the salen ligand structure on reaction rates and/or selectivities. This review article thus outlines the literature covering last five years, on the current developments of chiral polymetallic salen complexes used in asymmetric heterogeneous catalysis; their preparation, their efficiency as catalysts in various reactions and their recyclability are highlighted according to the immobilization procedures involved for their heterogenization. These methods include grafting on organic or inorganic supports insuring easy recovery by simple filtration. Polymerization processes are also part of recent research, leading to high densities of catalytic sites to favor their cooperativity. Combination of salen complexes via non covalent interactions or their introduction on MOFs and COFs networks is currently in full expansion, with examples of highly functionalized and enantioenriched products issued from tandem catalysis.

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Assembly of chiral monodentate ligands to chelates by donor–acceptor interactions

Cited by 23 publications

References 41 publications

Charge‐Transfer Interactions: An Efficient Tool for Recycling Bis(oxazoline)‐Copper Complexes in Asymmetric Henry Reactions

Charge‐Transfer Interactions: An Efficient Tool for Recycling Bis(oxazoline)‐Copper Complexes in Asymmetric Henry Reactions

Multiformat T‐Cell‐Engaging Bispecific Antibodies Targeting Human Breast Cancers

Chiral Salen Complexes for Asymmetric Heterogeneous Catalysis: Recent Examples for Recycling and Cooperativity

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