Diastereoselective synthesis of cis-N-Boc-4-aminocyclohexanol with reductive ring opening method using continuous flow

Szabó, Balázs; Tamás, Bálint; Faigl, Ferenc; Éles, János; Greiner, István

doi:10.1007/s41981-018-00028-3

Cited by 4 publications

(4 citation statements)

References 23 publications

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“…The implementation of flow technology allows for the rapid saturation of reaction media by making use of biphasic in-line mixing or gas-permeable membranes, leading to improved reaction kinetics. Devices such as the ThalesNano H-Cube ® [118,[224][225][226][227][228][229][230][231][232][233] (Figure 7) are used to effect highly efficient in-line mixing of hydrogen on a laboratory scale. Hydrogen is generated from electrolysis of water giving oxygen (or ozone) as a byproduct.…”

Section: Hydrogenationmentioning

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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Section: Hydrogenationmentioning

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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“…[172] The cycloaddition between 1,3-cyclohexadiene and Nsubstituted hydroxylamine combined with further reduction of the product in situ with MnO 2 , connected to a H-Cube® was recently disclosed. [173] A different approach allowed the synthesis of annulated pyridines in good to excellent yields through a cascade inverse-electron-demand HDA reaction and subsequent cycloreversion. The HDA reaction is assumed to occur via an intermediate tricyclic adduct which results from an intramolecular [4 + 2] cycloaddition across the C2 and C5 position of the pyrimidine ring followed by subsequent elimination of hydrogen cyanide.…”

Section: The Hetero Diels-alder (Hda) Reactionmentioning

confidence: 99%

“…The cycloaddition between 1,3‐cyclohexadiene and N ‐substituted hydroxylamine combined with further reduction of the product in situ with MnO 2 , connected to a H‐Cube® was recently disclosed . A different approach allowed the synthesis of annulated pyridines in good to excellent yields through a cascade inverse‐electron‐demand HDA reaction and subsequent cycloreversion.…”

Section: ‐Membered Ringsmentioning

confidence: 99%

Flow Chemistry for Cycloaddition Reactions

2020

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Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition reactions performed in flow systems. Cycloadditions are atom-efficient transformations for the synthesis of carbo-and heterocycles, involved in the construction of challenging skeletons of complex molecules. The main advantages of translating these processes into flow include using intensified conditions, safer handling of hazardous reagents and gases, easy tuning of reaction conditions, and straightforward scaling up. These benefits are especially important in cycloadditions such as the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder reaction, ozonolysis and [2 + 2] photocycloadditions. Some of these transformations are key reactions in the industrial synthesis of pharmaceuticals.

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“…Notably, hydrogenation reactions under continuous-flow are normally carried using 30 mm-long cartridge, as most of the catalysts are expensive or need time-consuming synthesis. [42][43][44][45][46][47] However, the H-Cube® Mini Plus allows to use 70-mm long cartridge, less reported in literature. 48,49 Journal Name…”

Section: Hydrogenation Testsmentioning

confidence: 99%

Scrap waste automotive converters as efficient catalysts for the continuous-flow hydrogenations of biomass derived chemicals

et al. 2020

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Diastereoselective synthesis of cis-N-Boc-4-aminocyclohexanol with reductive ring opening method using continuous flow

Cited by 4 publications

References 23 publications

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

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

Flow Chemistry for Cycloaddition Reactions

Scrap waste automotive converters as efficient catalysts for the continuous-flow hydrogenations of biomass derived chemicals

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