Synthesis of ?-nonalactone and ?-undecalactone

Nikishin, G. I.; Vorob'ev, V. D.

doi:10.1007/bf00920287

Cited by 1 publication

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“…The photoaddition of alcohols to 2 required an increased amount of BP, as expected from its lower electrophilicity. 9 With a BP/2 ratio of 0.4 to mediate the photoaddition of iPrOH, only 64% conversion was reached (entry 5). With a BP/2 ratio of 0.7, quantitative conversion was observed, and the corresponding product 4a was isolated in 52% yield (entry 6).…”

Section: ■ Introductionmentioning

confidence: 99%

Continuous-Flow Preparation of γ-Butyrolactone Scaffolds from Renewable Fumaric and Itaconic Acids under Photosensitized Conditions

Gérardy

Winter

Horn

et al. 2017

Org. Process Res. Dev.

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The method and results described herein concern the photosensitized addition of various alcohols to renewable platform fumaric and itaconic acids under scalable continuous-flow conditions in glass micro-and mesofluidic reactors. Alcohols were used both as reagents and as solvents, thus contributing to a reduced environmental footprint. Process parameters such as the temperature, light intensity, and the nature as well as amount of the photosensitizer were assessed under microfluidic conditions and, next, transposed to a lab-scale mesofluidic reactor connected with an in-line NMR spectrometer for real-time reaction monitoring. Substituted γ-butyrolactones, including spiro derivatives with unique structural features, were obtained with quantitative conversion of the starting materials and in 47−76% isolated yields. The model photoaddition of isopropanol to fumaric acid was next successfully transposed in a pilot-scale continuous-flow photoreactor to further demonstrate scalability.

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Section: ■ Introductionmentioning

confidence: 99%