Selective Addition of Carbamoylsilane to Vicinal Diketones: Highly Efficient Synthesis of β-Keto-α-hydroxyamides

AbstractA three-step batch-flow hybrid process has been developed for an expeditious synthesis of the enynol key intermediate of antifungal terbinafine. This procedure involves consecutive organometallic steps without the necessity of any in-line purification: after a metalation by n-butyllithium, a selective addition of the lithium salt was elaborated followed by a Grignard reaction resulting in a high yield of 6,6-dimethylhept-1-en-4-yn-3-ol. Moreover, as an alternative to tetrahydrofuran, cyclopentyl methyl ether was used as solvent implementing a safe, sustainable, yet selective synthetic process. Even on a laboratory-scale, the optimized batch-flow hybrid process had a theoretical throughput of 41 g/h. Furthermore, the newly developed process provides an efficient synthesis route to the key-intermediate, while making acrolein obsolete, minimizing side-products, and enabling safe and convenient scale-up.

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Highly efficient synthesis of rosuvastatin intermediate using a carboyl reductase‐cofactor co‐immobilized biocatalyst in the non‐aqueous biosystem

Journal of Chemical Technology & Biotechnology ◽

10.1002/jctb.6861 ◽

2021 ◽

Author(s):

Xiao‐Jian Zhang ◽

Di Wu ◽

Wen‐Zhong Wang ◽

Min Cao ◽

Qian Liu ◽

...

Keyword(s):

Efficient Synthesis ◽

Highly Efficient ◽

Immobilized Biocatalyst

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Sustainable production of γ-valerolactone and δ-valerolactone through the coupling of hydrogenation and dehydrogenation

Sustainable Energy & Fuels ◽

10.1039/d0se01776k ◽

2021 ◽

Author(s):

Hongxing Wang ◽

Guoqiang Ding ◽

Xianqing Li ◽

Haohao She ◽

Yulei Zhu ◽

...

Keyword(s):

Sustainable Production ◽

Efficient Synthesis ◽

Highly Efficient ◽

Catalytic Processes ◽

Lignocellulose Biomass

γ-valerolactone (GVL) and δ-valerolactone (DVL) are valuable chemicals that can be obtained by catalytic processes from nonedible lignocellulose biomass. However, highly efficient synthesis of GVL and DVL in an environmentally...

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Highly efficient synthesis of 5-hydroxymethylfurfural with carbohydrates over renewable cyclopentanone-based acidic resin

Green Chemistry ◽

10.1039/c7gc00673j ◽

2017 ◽

Vol 19 (8) ◽

pp. 1855-1860 ◽

Cited By ~ 21

Author(s):

Hao Tang ◽

Ning Li ◽

Fang Chen ◽

Guangyi Li ◽

Aiqin Wang ◽

...

Keyword(s):

Reusable Catalyst ◽

Efficient Synthesis ◽

Highly Efficient ◽

Acidic Resin

A sulfated cyclopentanone-formaldehyde condensate was found to be an effective and reusable catalyst for the dehydration of fructose to 5-hydroxymethylfurfural (HMF).

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