Asymmetric Organocatalysis in Continuous Flow: Opportunities for Impacting Industrial Catalysis

Atodiresei, Iuliana; Vila, Carlos; Rueping, Magnus

doi:10.1021/acscatal.5b00002

Cited by 189 publications

(81 citation statements)

References 57 publications

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“…[17][18][19][20][21][22][23][24][25][26][27][28][29] However, due to the extremelyf ast growthi no rganocatalyzed domino reactions,m anyn ew developments keep showing up on ad aily basis,w hich makes these reviews somewhat outdated very quickly.I na ddition, many of recentlyp ublished review articles on this topic are quite narrow in terms of theirs cope,f ocusing on either the synthesis of specific scaffolds or the processesm ediated by as pecific type of organocatalyst. [20][21][22][23][24][25][26][27][28][29] Due to the importance of this research and the fast developments in this area, we believe an ew review is needed and, in the present review,w ea re going to summarize the most recent developments in organocatalyzeda symmetric domino reactions,c overing the literature published from the beginning of 2012 up to May,2 017. Althoughs ome of the name reactions,such as the Mannich reactionand Biginelli reaction, are domino in nature,t hey are generally not covered in this review unless they are part of the entire domino reactions,b ecause there are many upto-date reviews out there dedicated to these name reactions.…”

Section: Introductionmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: Introductionmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…Accordingly, during the last fifteen years, the development of heterogeneous recyclable organocatalysts became a significant task. 16,32,[148][149][150][151][152] Moreover, several efficient organocatalysts were able to catalyse various reactions or could tolerate the presence of other catalytic species. Thus, their application in one-pot reactions also evolved rapidly.…”

Section: One-pot Reactions Using Heterogenized Chiral Organocatalystsmentioning

confidence: 99%

“…Furthermore, the successful recycling of these heterogeneous catalysts has promoted their application in continuous-flow systems. 190,191 Sequential asymmetric reactions using immobilized reagents, chiral organocatalysts and scavengers placed in successive fixed-bed reactors provided the opportunity for the convenient preparation of optically pure fine chemicals. Similar to the one-pot reactions, during these processes, several purification steps may be eliminated; moreover, reactions occurring through sensitive, unstable, hazardous intermediates are easily carried out.…”

Section: 186mentioning

confidence: 99%

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

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The preparation of optically pure fine chemicals is among the most important and challenging tasks met by organic chemists. Recently, significant efforts have been focused on the development of green and sustainable procedures for the synthesis of these high value-added compounds. Asymmetric heterogeneous catalysis has provided efficient solutions to these challenges. The application of heterogeneous chiral catalysts in one-pot processes combines the advantages of use of these materials with time, material, and energy savings associated with cascade or sequential procedures. This review surveys these asymmetric onepot reactions reported until July 2017, in which a heterogeneous chemical catalyst has been applied either as a single multifunctional catalyst or in combination with a second catalytically active material. These processes include one-pot procedures catalysed by carefully designed solids obtained by the immobilization of chiral metal complexes, by anchoring chiral organocatalysts, or by modifying catalytic surfaces with optically pure compounds, which may also incorporate uncatalyzed and homogeneously catalysed steps. Methods applying achiral heterogeneous catalysts in combination with soluble chiral chemical catalysts or biocatalysts are also presented. Sophisticated, finely tuned materials have been applied in most of these reactions, which have been discussed along with the main requirements necessary to perform these transformations in a one-pot manner.

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“…[1][2][3][4] However, trickle-bed reactors and slurry bubble columns are still the workhorses in the chemical industry for multiphase operations involving heterogeneously catalyzed reactions with gas-liquid reactants. While stirring in the slurry reactor prevents catalyst particles from settling and allows active mixing at high Reynolds numbers (minimizing temperature and concentration gradients), subsequent separation of the catalyst particles and partial replacement due to damage from attrition is required.…”

Section: Introductionmentioning

confidence: 99%

High-performance monoliths in heterogeneous catalysis with single-phase liquid flow

et al. 2017

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Hierarchical, macro-mesoporous silica monoliths with domain sizes (sum of mean macropore size and skeleton thickness) of ∼1 μm are highly efficient supports in heterogeneous catalysis with single-phase liquid flow. Their unprecedented performance regarding low backmixing, the elimination of internal and external diffusive transport limitations, as well as the simultaneous realization of a large (internal and external) surface area of the monolith skeleton allow reactor operation under exclusive reaction control. For experimental characterization, the Knoevenagel condensation was employed with an aminopropylated silica monolith integrated into an on-line coupled, high-pressure reaction-analysis system. It allows precise, fully automated adjustment and control of all relevant reaction parameters and promises a boost in the rapid, reproducible determination of the intrinsic reaction kinetics, in general. Hydrodynamic and reaction kinetic parameters identify extreme plug-flow conditions with this high-surface-area, compact type of microreactor and quasi-homogeneous operation in continuous-flow mode.

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Asymmetric Organocatalysis in Continuous Flow: Opportunities for Impacting Industrial Catalysis

Cited by 189 publications

References 57 publications

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

High-performance monoliths in heterogeneous catalysis with single-phase liquid flow

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