Synthesis of 1,2,3,4‐Tetrahydroisoquinolines by Microreactor‐Mediated Thermal Isomerization of Laterally Lithiated Arylaziridines

Giovine, Arianna; Musio, Biagia; Degennaro, Leonardo; Falcicchio, Aurelia; Nagaki, Aiichiro; Yoshida, Jun‐ichi; Luisi, Renzo

doi:10.1002/chem.201203533

Cited by 52 publications

(28 citation statements)

References 40 publications

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“…Luisi and Yoshida reported another example of reaction pathways switch exploiting a thermally induced isomerization of laterally lithiated aziridines [27]. In this report, taking advantage of the exquisite temperature control realized in flow microreactors, either functionalized arylaziridines or 1,2,3,4-tetrahydroisoquinolines (THIQs) were synthesized.…”

Section: Methodsmentioning

confidence: 99%

Flow Technology for Organometallic-Mediated Synthesis

Degennaro¹,

Carlucci²,

Angelis³

et al. 2016

J Flow Chem

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Section: Methodsmentioning

confidence: 99%

Flow Technology for Organometallic-Mediated Synthesis

Degennaro¹,

Carlucci²,

Angelis³

et al. 2016

J Flow Chem

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“…For example, microreactors have been used to prepare enantiomerically pure products [24,25], fluoro-organic compounds [26][27][28][29], β-peptides [30], tetrahydroisoquinolines [31], and 2-aminothiazoles via the Hantzsch reaction [32]. The Koch-Haaf carboxylation of adamantanols is also described [33].…”

Section: Microreactors In Chemistrymentioning

confidence: 99%

Enzymatic microreactors in biocatalysis: history, features, and future perspectives

Laurenti¹,

Vianna²

2016

Biocatalysis

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Microfluidic reaction devices are a very promising technology for chemical and biochemical processes. In microreactors, the micro dimensions, coupled with a high surface area/volume ratio, permit rapid heat exchange and mass transfer, resulting in higher reaction yields and reaction rates than in conventional reactors. Moreover, the lower energy consumption and easier separation of products permit these systems to have a lower environmental impact compared to macroscale, conventional reactors. Due to these benefits, the use of microreactors is increasing in the biocatalysis field, both by using enzymes in solution and their immobilized counterparts. Following an introduction to the most common applications of microreactors in chemical processes, a broad overview will be given of the latest applications in biocatalytic processes performed in microreactors with free or immobilized enzymes. In particular, attention is given to the nature of the materials used as a support for the enzymes and the strategies employed for their immobilization. Mathematical and engineering aspects concerning fluid dynamics in microreactors were also taken into account as fundamental factors for the optimization of these systems.

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“…The flow microreactor method can also be applied to the generation and reactions of α-triphenylsilyloxiranyllithium from epoxyethyltriphenylsilane and aziridinyllithiums from N-Bus-aziridines and N-tosylaziridines [56][57][58][59]. Recently, the efficient and highly reproducible synthesis of functionalized aziridines and 1,2,3,4-tetrahydroisoquinolines (THIQs) has also been reported [60].…”

Section: Control Of Unstable Organolithiums Using Flow Microreactorsmentioning

confidence: 99%