Stereoselectivity Inversion by Water Addition in the −SO3H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives

Alexander Yu Sidorenko, Nikolai S. Li-Zhulanov, Päivi Mäki-Arvela, Thomas Sandberg, Anna V. Kravtsova, Andreia F. Peixoto, Cristina Freire, Konstantin P. Volcho, Nariman F. Salakhutdinov, Vladimir E. Agabekov, Dmitry Yu Murzin

Результат исследования: Научные публикации в периодических изданияхстатья

1 Цитирования (Scopus)

Аннотация

A range of heterogeneous -SO3H functionalized catalysts including carbon and halloysite nanotubes, commercial K10 clay, Amberlyst-15 etc. was investigated for the first time using as a model the Prins-Ritter reaction of (−)-isopulegol with benzaldehyde and acetonitrile producing 4-amido derivatives of octahydro-2H-chromenes (as (S)- and (R)-diastereomers). A strong effect of water addition prior the reaction on the overall selectivity and the ratio of isomers in the case of heterogeneous and homogeneous (p-toluenesulfonic acid) catalysis was found for the first time. The yield of the (R)-diastereomer sharply increased with increasing amount of added water, while the S-isomer prevailed with a minimum amount of added water. Experimental results and DFT calculations clearly indicate a kinetic control for R-amide formation. Typically synthesis of 4-amidooctahydro-2H-chromenes requires subzero temperatures and toxic catalysts, which were avoided in the current work. Nevertheless, the yield of the desired products (up to 83 %) at 30 °C after water addition exceeded the values reported previously. Thus, adding water is a simple and a very effective method for controlling both the yield and stereoselectivity of the Prins-Ritter reaction products under mild conditions.

Язык оригиналаанглийский
Страницы (с-по)2605-2609
Число страниц5
ЖурналChemCatChem
Том12
Номер выпуска9
DOI
СостояниеОпубликовано - 7 мая 2020

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  • Цитировать

    Sidorenko, A. Y., Li-Zhulanov, N. S., Mäki-Arvela, P., Sandberg, T., Kravtsova, A. V., Peixoto, A. F., Freire, C., Volcho, K. P., Salakhutdinov, N. F., Agabekov, V. E., & Murzin, D. Y. (2020). Stereoselectivity Inversion by Water Addition in the −SO3H-catalyzed Tandem Prins-Ritter Reaction for Synthesis of 4-amidotetrahydropyran Derivatives. ChemCatChem, 12(9), 2605-2609. https://doi.org/10.1002/cctc.202000070