Mixing and matching chiral cobalt- and manganese-based calix-salen catalysts for the asymmetric hydrolytic ring opening of epoxides

Dandachi, Hiba; Zaborova, Elena; Kolodziej, Emilie; David, Olivier; Hannedouche, Jérôme; Mellah, Mohamed; Jaber, Nada; Schulz, Emmanuelle

doi:10.1016/j.tetasy.2016.02.006

Cited by 12 publications

(11 citation statements)

References 34 publications

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“…We were pleased to show that this heterobimetallic system was not only efficient in homogeneous catalysis, but could be also applied to heterogeneous conditions. As previously reported, [53] we prepared Co‐salen complexes embedded into macrocyclic calixarenic‐like structures, and their Mn−Cl analogues were accordingly synthesised in high yields [65] . Both complexes were engaged together as heterogeneous catalysts to promote the DKR of epibromohydrin.…”

Section: Cobalt‐salen Complexes Intimately Associated With Epoxides mentioning

confidence: 91%

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Chiral Cobalt‐Salen Complexes: Ubiquitous Species in Asymmetric Catalysis

Schulz

2021

The Chemical Record

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Since the discovery of their extraordinary reactivity in the hydrolytic kinetic resolution of terminal epoxides about twenty years ago, chiral cobalt‐salen complexes have been shown to be essential for many other asymmetric catalytic reactions. This account summarizes the inspiring works dedicated to the discovery of their new reactivity and their mode of action, as well as the new processes towards the optimization of their cooperativity for bimetallic activation and the implementation of their effective immobilization, including also our contribution on these topics.

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Section: Cobalt‐salen Complexes Intimately Associated With Epoxides mentioning

confidence: 91%

“… DKR of epibromohydrin under heterogeneous conditions with a mixture of homometallic macrocyclic Co‐salen complexes [65] …”

Section: Cobalt‐salen Complexes Intimately Associated With Epoxides mentioning

confidence: 99%

Chiral Cobalt‐Salen Complexes: Ubiquitous Species in Asymmetric Catalysis

Schulz

2021

The Chemical Record

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“…In this context, we also prepared manganesecontaining calixsalen complexes; whereas they showed no activity in the hydrolysis of meso epoxides, the use of a 1/1 mixture of Mn-and Comacrocycles delivered the targeted diol with a higher enantioselectivity than that obtained in the presence of the unique cobalt complex (see scheme 10). [30] Scheme 10: Hydrolysis of cyclohexene oxide by Co-and Mn-calixsalen complexes Indeed cooperativity between the Co-and Mncontaining catalysts was obvious, at least when the introduced species possessed the same configuration at the stereogenic centers. As can be seen in Scheme 10 for instance, opening of cyclopentenoxide occurred with both a large activity and selectivity enhancement with the dual activation, as a match combination.…”

Section: Scheme 9: Dynamic Hkr Of Epibromohydrin With Co III -Calixsamentioning

confidence: 99%

Chiral salen complexes in polymeric main‐chains for heterogeneous asymmetric catalysis – a brief account

Dandachi

Hong

Ibrahim

et al. 2020

Vietnam Journal of Chemistry

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This brief account summarizes our contribution to the field of heterogeneous asymmetric catalysis with salen complexes. We have developed two different procedures to immobilize these highly efficient catalysts in polymeric main chains for multiple reasons. These heterogenized structures possess indeed solubility properties allowing their easy recovery by simple filtration. Furthermore, by avoiding the use of large either organic or inorganic supports, the introduced catalytic mass does not so much differ from the homogeneous one. Finally, catalytic sites location is precisely controlled, a parameter of major importance for some reactions in which bimetallic activation is needed. Their use and efficiency as insoluble catalysts is here described for the promotion of C‐O and C‐C bonds formation, with a specific emphasis on their reusability and cooperativity.

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“…Moreover, the use of heterobimetallic catalytic systems was particularly effective to promote the opening of meso ‐epoxides and the HKR of epibromohydrin, with a match effect by using an equivalent catalytic mixture of Co‐ and Mn‐based calix‐salen having the same configuration (eq b), Scheme ). In addition, this recycled mixture was further reused for subsequent runs without need of any cobalt reactivation step …”

Section: Macrocyclic Salen Complexesmentioning

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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Mixing and matching chiral cobalt- and manganese-based calix-salen catalysts for the asymmetric hydrolytic ring opening of epoxides

Cited by 12 publications

References 34 publications

Chiral Cobalt‐Salen Complexes: Ubiquitous Species in Asymmetric Catalysis

Chiral Cobalt‐Salen Complexes: Ubiquitous Species in Asymmetric Catalysis

Chiral salen complexes in polymeric main‐chains for heterogeneous asymmetric catalysis – a brief account

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

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