Recyclable Organocatalysts in Asymmetric Reactions

Gruttadauria, Michelangelo; Giacalone, Francesco; Noto, Renato

doi:10.1002/9781118087992.ch2

Cited by 14 publications

(8 citation statements)

References 209 publications

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“…Several recent review articles related to this subject have been published. 2,[5][6][7][8][9][10] Most of these are focused on polymers that are covalently bonded to the chiral organocatalyst. A review of chiral organocatalysts that are linked to the support with a non-covalent bond is also available.…”

Section: Polymer-immobilized Chiral Organocatalystsmentioning

confidence: 99%

Polymer-immobilized chiral catalysts

Itsuno

Hassan

2014

RSC Adv.

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This review illustrates the current strategies and potential of polymer-immobilized chiral catalysts for highly enantioselective asymmetric synthesis. Abstract:Polymer immobilization of chiral catalysts has progressed extensively over the past years. Recent intensive development of chiral organocatalysts resulted in the identification of numerous highly active catalysts, which are, however, still far less effective than transition metal catalysts. Separation of relatively large amounts of organocatalysts from the reaction mixture causes problems during product isolation. In the case of chirally modified metal catalysts, recovery of the valuable metal species and suppression of metal leaching are perpetually important requirements in the design of environmentally friendly chemical processes. Various types of chiral organocatalysts and metal catalysts have been immobilized as pendant groups onto the side chains of polymer supports. Another important polymer immobilization technique is the incorporation of a chiral catalyst into its main chain, with several types of chiral catalyst monomers having been copolymerized with achiral monomers for their production.Recently, the synthesis of chiral main-chain polymeric catalysts has progressed extensively. Moreover, many examples of polymer-immobilized catalysts exhibited higher enantioselectivities in comparison to those of the corresponding low-molecular-weight catalyst. The development of these polymer-immobilized chiral

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Section: Polymer-immobilized Chiral Organocatalystsmentioning

confidence: 99%

Polymer-immobilized chiral catalysts

Itsuno

Hassan

2014

RSC Adv.

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“…Herein we describe the development of a new adaptable microgel-based colloidal catalyst system. In this system the microgels act as reactive carriers for covalently attached organocatalysts . The particular microgel design allows the catalyst system to remain swollen and colloidally stable at higher reaction temperatures, while a reduction in temperature leads to a volume phase transition that induces shrinkage of microgels and precipitation from the reaction mixture (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Reversible Switching and Recycling of Adaptable Organic Microgel Catalysts (Microgelzymes) for Asymmetric Organocatalytic Desymmetrization

et al. 2018

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Adaptable enzyme-mimetic catalysts based on temperature-responsive polymer microgels (microgelzymes) have been developed. By a simple change in the temperature, a microgel catalyst can be reversibly switched into its soluble or precipitated form, thus combining the advantages of homogeneous and heterogeneous catalysis. The responsive microgel reactors show high reactivity and selectivity, as well as good recycling properties in the alcoholysis of cis-tetrahydrophthalic anhydride.

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“…Organocatalysis is a useful synthetic method also applied in asymmetric reactions and polymer immobilization of chiral catalysts is still a topic of interest [46,47]. In this section, one example of asymmetric α-amination of 1,3-dicarbonyl compounds and some examples of C-C forming reactions including aza-Henry reaction, Michael addition, α-alkylation of aldehyde, Diels-Alder reaction and aldol reaction, are reported.…”

Section: Organocatalysed Asymmetric Reactionsmentioning

confidence: 99%

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

2016

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Abstract:In this review, the most recent advances (2014)(2015)(2016) on the synthesis of new polymer-supported catalysts are reported, focusing the attention on the synthetic strategies developed for their preparation. The polymer-supported catalysts examined will be organic-based polymers and organic-inorganic hybrids and will include, among others, polystyrenes, poly-ionic liquids, chiral ionic polymers, dendrimers, carbon nanotubes, as well as silica and halloysite-based catalysts. Selected examples will show the synthesis and application in the field of organocatalysis and metal-based catalysis both for non-asymmetric and asymmetric transformations.

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Recyclable Organocatalysts in Asymmetric Reactions

Cited by 14 publications

References 209 publications

Polymer-immobilized chiral catalysts

Polymer-immobilized chiral catalysts

Reversible Switching and Recycling of Adaptable Organic Microgel Catalysts (Microgelzymes) for Asymmetric Organocatalytic Desymmetrization

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

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