Continuous flow based catch and release protocol for the synthesis of α-ketoesters

Palmieri, Alessandro; Ley, Steven V.; Polyzos, Anastasios; Ladlow, Mark; Baxendale, Ian R.

doi:10.3762/bjoc.5.23

Cited by 38 publications

(14 citation statements)

References 102 publications

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“…A mixed acid/base scavenger work‐up was then used to remove the base, excess carboxylic acid and by‐products. For nitrogen‐containing heterocyclic carboxylic acid starting materials it was found necessary to use a catch‐and‐release protocol to afford the purified products.…”

Section: Flow Chemistry: Backgroundmentioning

confidence: 99%

The integration of flow reactors into synthetic organic chemistry

Baxendale

2013

J of Chemical Tech & Biotech

244

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The material presented in this review is based upon discussions and interactions with members of the Department of Chemistry and Biochemistry within the University of Windsor, Ontario, Canada. This article explores the changing face of chemical synthesis with regard to the impact of flow based chemical processing technologies. Highlighted works from the Innovative Technology Centre (ITC), Cambridge, UK, are used to illustrate the alternative synthetic practices available to modern research chemists. The dominant theme of the review is the synergistic effects encountered by combining the advantages of continuous processing regimes with the power of immobilized reagents and scavenger systems for multi‐step organic chemistry. © 2012 Society of Chemical Industry

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Section: Flow Chemistry: Backgroundmentioning

confidence: 99%

The integration of flow reactors into synthetic organic chemistry

Baxendale

2013

J of Chemical Tech & Biotech

244

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“…α-keto ester 5 (Scheme 2). [11] For the second silylation the use of LiTMP as a base was required, since other bases did not deliver any product.…”

Section: Resultsmentioning

confidence: 99%

Continuous Flow Synthesis of Highly Substituted Tetrahydrofurans

Hoffmeyer

Schneider

2019

Eur J Org Chem

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The highly diastereoselective synthesis of multiply substituted tetrahydrofurans was achieved in a sequential process under continuous flow conditions. Greatly reduced reaction times, improved selectivities and enhanced yields are the benefits of this approach in comparison to the initial batch synthesis. Moreover, gram amounts of product were produced in the flow reactor likewise due to facile upscaling. In addition, employing a novel bis(silyl)dienediolate tetrasubstituted tetrahydrofurans were made accessible as well.

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“…Because of their importance, in 2009, Ley et al. developed a new and practical flow‐chemical conversion of β‐nitroacrylates into α‐keto esters . The method involves three different transformations that, thanks to the use of a Uniqsis FlowSynTM device, are performed in succession (Scheme ).…”

Section: Addition Of Nucleophiles To β‐Nitroacrylatesmentioning

confidence: 99%

β‐Nitroacrylates: A Versatile and Growing Class of Functionalized Nitroalkenes

2018

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b-Nitroacrylatesa re an important subclass of nitroolefins in which an ester and an itro group are simultaneously linked, in a-a nd b-positions,t oa doubleb ond. This peculiarity makes these nitro derivatives highly reactivew ith ap lethorao fn ucleophiles,v ery often under extremely mild reaction conditions, andt hust hey can serve as excellent building blocks towards highly functionalized materials. Basedo nt he growing applicationo fb-nitroacrylates in organic synthesis,w ec onsidered it to be useful to highlight in this review the most important results obtained over the last ten years.

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Continuous flow based catch and release protocol for the synthesis of α-ketoesters

Abstract: SummaryUsing a combination of commercially available mesofluidic flow equipment and tubes packed with immobilised reagents and scavengers, a new synthesis of α-ketoesters is reported.

Cited by 38 publications

References 102 publications

The integration of flow reactors into synthetic organic chemistry

The integration of flow reactors into synthetic organic chemistry

Continuous Flow Synthesis of Highly Substituted Tetrahydrofurans

β‐Nitroacrylates: A Versatile and Growing Class of Functionalized Nitroalkenes

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