Upgrading furanic platforms to α-enaminones: tunable continuous flow hydrogenation of bio-based cyclopentenones

文献情報

出版日 2022-11-24

DOI 10.1039/D2RE00292B

インパクトファクター 4.239

著者

Lídia A. S. Cavaca, Jaime A. S. Coelho, Susana D. Lucas, Rui M. S. Loureiro, Rafael F. A. Gomes, Carlos A. M. Afonso

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要旨

Here we describe a tunable continuous flow hydrogenation of trans-4,5-diamino cyclopentenones (DCPs) allowing the selective stepwise synthesis of novel bifunctionalized cyclopentanones (up to 96% yield and >92% selectivity). Stability studies of the diamino cyclopentanone motif led to the development of an elimination procedure yielding the corresponding α-enaminones in good yields. Deuteration of the cyclopentene scaffold can also be performed using D2O as a source of D2. A sequential process for the synthesis of α-enaminones directly from furfural is also described. The methodology allows the preparation of a previously reported ATP-sensitive potassium channel agonist in 71% yield.

掲載誌

Reaction Chemistry & Engineering

CiteScore: 0

自己引用率: 8.8%

年間論文数: 284

Reaction Chemistry & Engineering is an interdisciplinary journal reporting cutting-edge research focused on enhancing the understanding and efficiency of reactions. Reaction engineering leverages the interface where fundamental molecular chemistry meets chemical engineering and technology. Challenges in chemistry can be overcome by the application of new technologies, while engineers may find improved solutions for process development from the latest developments in reaction chemistry. Reaction Chemistry & Engineering is a unique forum for researchers whose interests span the broad areas of chemical engineering and chemical sciences to come together in solving problems of importance to wider society. All papers should be written to be approachable by readers across the engineering and chemical sciences. Papers that consider multiple scales, from the laboratory up to and including plant scale, are particularly encouraged.

Upgrading furanic platforms to α-enaminones: tunable continuous flow hydrogenation of bio-based cyclopentenones

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