An Asymmetric Organocatalytic Aldol Reaction of a Hydrophobic Aldehyde in Aqueous Medium Running in Flow Mode

Schober, Lukas; Ratnam, Shahilan; Yamashita, Yasunobu; Adebar, Niklas; Pieper, Matthias; Berkessel, Albrecht; Hessel, Volker; Gröger, Harald

doi:10.1055/s-0037-1610404

Cited by 15 publications

(11 citation statements)

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“…Representing a major mode of carbon-carbon bond formation, aldol addition is an appealing tool that has been broadly used in chemical and synthetic biology research [1][2][3]. Important applications include chemo-enzymatic synthesis of chiral synthons and bioactive chemicals [4][5][6][7][8][9][10], as well as labelling of biomolecules (protein, DNA and RNA) [3,11]. Given its usefulness, different approaches have been developed to mediate aldol addition [4,[12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…Important applications include chemo-enzymatic synthesis of chiral synthons and bioactive chemicals [4][5][6][7][8][9][10], as well as labelling of biomolecules (protein, DNA and RNA) [3,11]. Given its usefulness, different approaches have been developed to mediate aldol addition [4,[12][13][14][15][16]. Naturally occurring and de novo aldolases are excellent options.…”

Section: Introductionmentioning

confidence: 99%

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Streptavidin-Hosted Organocatalytic Aldol Addition

2020

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In this report, the streptavidin-biotin technology was applied to enable organocatalytic aldol addition. By attaching pyrrolidine to the valeric motif of biotin and introducing it to streptavidin (Sav), a protein-based organocatalytic system was created, and the aldol addition of acetone with p-nitrobenzaldehyde was tested. The conversion of substrate to product can be as high as 93%. Although the observed enantioselectivity was only moderate (33:67 er), further protein engineering efforts can be included to improve the selectivity. These results have proven the concept that Sav can be used to host stereoselective aldol addition.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Streptavidin-Hosted Organocatalytic Aldol Addition

2020

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“…As biocatalysis is becoming more and more important, one of the major issues is the solvent usage. Water is not usually the media of choice to perform organic reactions, therefore, the group of Gröger created a proof-of-concept apparatus capable of subsequently being telescoped directly into a biocatalysed process [ 104 ].…”

Section: Reviewmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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“…The most straightforward options are microcapillaries with internal diameters ranging from hundreds of microns to millimeters connected by commercially available PEEK (polyether ether ketone) or steel connectors, among other materials, [17][18][19]38,39,41,[47][48][49][51][52][53][57][58][59][60]66,69] as shown in Figure 1(a). Fluoropolymers, such as PTFE (polytetrafluoroethylene), [18,38,39,49,53,58,66] perfluoroalkoxy polymer, [52] and fluorinated ethylene-propylene, [17] remain the most popular microcapillary materials for their excellent chemical resistance and relatively high melting points. Borosilicate glass [48,69] and fused silica capillaries [19,47,51] are transparent and chemically and thermally resistant.…”

Section: Reactor Materials and Designmentioning

confidence: 99%

“…These microreactors contain one, two, or more phases, which actively participate in a chemical reaction. A similar number of studies have focused on homogeneous (single-phase) [15,16,[38][39][40][41]45,48,49,52,53,57,[59][60][61]65,73] and heterogeneous (multiphase) reactors, [17][18][19][20][42][43][44]47,50,51,54,56,58,[62][63][64][66][67][68][69][70][71][72]74,76,77] as outlined in Table 1.…”

Section: Microreactors and Their Benefits For Enantiomer And Diastereoisomer Synthesismentioning

confidence: 99%

Microreaction and membrane technologies for continuous single-enantiomer production: A review

et al. 2021

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Microreaction and membrane technologies offer optimal conditions for controlling enantiomer synthesis and purification processes in continuous production, with numerous advantages over batch manufacturing. One of the many forces driving the development of such technologies for the production of single optical isomers is the need for enantiomerically pure pharmaceutical drugs because enantiomers may display opposite therapeutic effects or different treatment efficacies and side effects. Yet, despite advances in asymmetric synthesis and separation techniques, preparing enantiomerically pure compounds remains a challenging task. Here, we review the progress in microfluidics and membrane chiral separation over the last two decades. In addition to describing and critically assessing the state of the art in both disciplines, we provide an overview of their beneficial properties and characteristics for developing technologies toward producing enantiomerically pure compounds. Concomitantly, we evaluate efforts to integrate synthesis and membrane separation into a microfluidic platform and pinpoint the limiting factors that must be overcome before these platforms can be fully deployed in the industry.

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An Asymmetric Organocatalytic Aldol Reaction of a Hydrophobic Aldehyde in Aqueous Medium Running in Flow Mode

Cited by 15 publications

References 0 publications

Streptavidin-Hosted Organocatalytic Aldol Addition

Streptavidin-Hosted Organocatalytic Aldol Addition

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Microreaction and membrane technologies for continuous single-enantiomer production: A review

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