Large‐Scale Applications of Organocatalysis

Berkessel, Albrecht; Gröger, Harald

doi:10.1002/3527604677.ch14

Cited by 3 publications

(1 citation statement)

References 18 publications

(29 reference statements)

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“… 6 Consequently, this makes the reaction setup less complex and, therefore, makes it possible to consider these reactions for manufacturing processes. 7 , 8 , 9 , 10 Since the pioneering work of the immobilization of proline onto a polymer support, 11 the field of the incorporation of chiral aminocatalysts on solid supports has begun to develop fast. Many examples are available for the successful use of both soluble and insoluble polymer-supported iminium-activation-based catalysts, especially prolines, imidazolidinones and their derivatives in different types of catalytic reactions.…”

Section: Introductionmentioning

confidence: 99%

Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

Murre,

Mikli,

Erkman

et al. 2023

iScience

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Section: Introductionmentioning

confidence: 99%

Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

Murre,

Mikli,

Erkman

et al. 2023

iScience

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Switchable‐Hydrophilicity Solvents for Product Isolation and Catalyst Recycling in Organocatalysis

et al. 2016

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Switchable‐hydrophilicity solvents (SHSs) are solvents that can switch reversibly between a water‐miscible state to a state that forms a biphasic mixture with water. In this case study, SHSs have been studied for easy product/catalyst separation as well as catalyst recycling. A series of tertiary amine SHSs have been identified for the extraction of the hydrophilic product from the postreaction mixture. Here, we determined high extraction efficiencies for the product (>84 %) and low extraction rates for the catalyst (<0.1 %). With the catalyst recycling experiments, we isolated the product in high purity (>98 %) without further purification steps. At the same time, the catalyst was reused without any loss of activity (>91 % enantiomeric excess, >99 % yield) four times. Furthermore, we optimized the extraction efficiency by working with a microextractor. In addition, with the use of a falling‐film microreactor, we obtained the product with high enantioselectivity by working at ambient conditions.

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Simple and Effective Catalyst Separation by New CO₂‐Induced Switchable Organocatalysts

Großeheilmann

Kragl

2017

ChemSusChem

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CO -induced switchable tertiary amine-based organocatalysts were investigated for an efficient catalyst and product separation by its different partitioning between an organic and carbonated water phase. In this case study, the switching ability of eight tertiary amine-based catalysts between the organic and water phase by addition or removal of CO was investigated. Here, the catalyst switched both nearly completely (99.9 %) into the aqueous phase by addition of CO and effectively back into the organic phase (99.3 %) by expelling CO . With this technique, the organocatalyst was successfully recovered and reused twelve times without significant loss of activity (up to 90 % enantiomeric excess) for the asymmetric nitroaldol (Henry) reaction. After the first catalyst switch, evaporation of the solvent affords the product in 98 % purity without any further purification steps.

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Large‐Scale Applications of Organocatalysis

Cited by 3 publications

References 18 publications

Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

Switchable‐Hydrophilicity Solvents for Product Isolation and Catalyst Recycling in Organocatalysis

Simple and Effective Catalyst Separation by New CO₂‐Induced Switchable Organocatalysts

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Large‐Scale Applications of Organocatalysis

Cited by 3 publications

References 18 publications

Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

Switchable‐Hydrophilicity Solvents for Product Isolation and Catalyst Recycling in Organocatalysis

Simple and Effective Catalyst Separation by New CO2‐Induced Switchable Organocatalysts

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Simple and Effective Catalyst Separation by New CO₂‐Induced Switchable Organocatalysts