Photochemical In-Flow Synthesis of 2,4-Methanopyrrolidines: Pyrrolidine Analogues with Improved Water Solubility and Reduced Lipophilicity

Levterov, Vadym V.; Michurin, Oleg M.; Borysko, Petro; Zozulya, Sergey; Sadkova, Iryna V.; Tolmachev, Andrey A.; Mykhailiuk, Pavel K.

doi:10.1021/acs.joc.8b02071

Cited by 73 publications

(45 citation statements)

References 71 publications

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“…92 For instance, introduction of a stereocenter in compound 2.9 did not significantly affect the log P, however it drastically lowered the melting point thus indicating a significantly less stable crystal lattice and better solubility in water (Fig. 8C) 39,93,94 (see chapter 3 in ref. 60).…”

Section: Disruption Of Planarity and Symmetrymentioning

confidence: 97%

Molecular photoswitches in aqueous environments

et al. 2021

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Section: Disruption Of Planarity and Symmetrymentioning

confidence: 97%

Molecular photoswitches in aqueous environments

et al. 2021

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“…2,4-Methanopyrrolidines are an important heterocyclic class of compounds that display higher hydrophilicity than regular pyrrolidines. Several applications demonstrate that their continuous photochemical synthesis based on an intramolecular [2 + 2] cycloaddition ( Figure 11A) can be scaled to kilogram quantities in order to facilitate further derivatization [31,62,63]. The synthesis of 3-hydroxyazetidines via a continuous Norrish-Young photocyclization reaction ( Figure 11B) represents a further demonstration of effectively creating drug-like structures in a simple and atom-economical fashion, and a recent study reports on the versatility of this transformation [64].…”

Section: Synthesis Of Bioactives: Drugs and Natural Productsmentioning

confidence: 99%

Continuous Flow Photochemistry for the Preparation of Bioactive Molecules

2020

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The last decade has witnessed a remarkable development towards improved and new photochemical transformations in response to greener and more sustainable chemical synthesis needs. Additionally, the availability of modern continuous flow reactors has enabled widespread applications in view of more streamlined and custom designed flow processes. In this focused review article, we wish to evaluate the standing of the field of continuous flow photochemistry with a specific emphasis on the generation of bioactive entities, including natural products, drugs and their precursors. To this end we highlight key developments in this field that have contributed to the progress achieved to date. Dedicated sections present the variety of suitable reactor designs and set-ups available; a short discussion on the relevance of greener and more sustainable approaches; and selected key applications in the area of bioactive structures. A final section outlines remaining challenges and areas that will benefit from further developments in this fast-moving area. It is hoped that this report provides a valuable update on this important field of synthetic chemistry which may fuel developments in the future.

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“…To overcome these problems, thin, low volume glassware has been developed, however, only small batches can be run resulting in low productivity. For these reasons, microfluidic flow reactor technology has been shown to be a good fit to reduce the reaction times and increase the efficiency, therefore gaining the desired throughputs [495][496][497]. Many examples of customised flow photoreactors have been developed and investigated for [2 + 2] cycloadditions [316,[498][499][500][501][502][503][504][505][506].…”

Section: Cycloaddition Reactionsmentioning

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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Photochemical In-Flow Synthesis of 2,4-Methanopyrrolidines: Pyrrolidine Analogues with Improved Water Solubility and Reduced Lipophilicity

Cited by 73 publications

References 71 publications

Molecular photoswitches in aqueous environments

Molecular photoswitches in aqueous environments

Continuous Flow Photochemistry for the Preparation of Bioactive Molecules

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

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