Catalytic condensation of α-pinene with formaldehyde

Sidorenko, A.Yu.; Kurban, Yu.M.; Il'ina, I.V.; Li-Zhulanov, N.S.; Patrusheva, O.S.; Goltsova, V.V.; Bei, M.P.; Aho, A.; Wärnå, J.; Heinmaa, I.; Kouznetsova, T.F.; Volcho, K.P.; Salakhutdinov, N.F.; Murzin, D.Yu.; Agabekov, V.E.

doi:10.1016/j.jcat.2024.115306

Cited by 6 publications

(4 citation statements)

References 52 publications

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“… However, under these conditions we obtained (−)-terpinyl acetate (−)- 18 as the main product (Scheme ). Small amount of (−)-8-acetoxy-6-hydroxymethyllimonene (−)- 17 we recently described was formed as well. Interestingly, we did not observe formation of (−)-6-hydroxymethyllimonene (−)- 12 or acetate 16 .…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, we did not observe formation of (−)-6-hydroxymethyllimonene (−)- 12 or acetate 16 . Optimal conditions for the synthesis of 8-acetoxy-6-hydroxymethyllimonene (−)- 17 were previously described by us in and involved the interaction of (−)-α-pinene (−)- 15 and paraform for 6 h at 8 °C in the presence of glacial acetic and orthophosphoric acids. Under these conditions, the amount of (−)-8-acetoxy-6-hydroxymethyllimonene acetate (−)- 17 and (−)-terpinyl acetate (−)- 18 in the reaction mixture was 20 and 35%, respectively (GC–MS data).…”

Section: Resultsmentioning

confidence: 99%

“…Because acetate (−)- 17 decomposes under vacuum distillation, it was isolated by Column chromatography (CC) on silica gel. The final yield of acetate (−)- 17 was 19% . It should be noted that direct hydroxymethylation of limonene 9 leads to the formation of a large number of compounds that, according to GC–MS data, are products of the Prins reaction (more than 20 compounds with m / z = 166, 178, 208).…”

Section: Resultsmentioning

confidence: 99%

“…CH 2 Cl 2 was passed through calcined Al 2 O 3 . (−)-8-Acetoxy-6-hydroxymethyllimonene (−)- 17 have been synthesized according to from (−)-α-pinene (98.0%, Aldrich). CC: silica gel (SiO 2 ; 60–200 μ; Macherey-Nagel); hexane/EtOAc 100:0 → 0:100.…”

Section: Methodsmentioning

confidence: 99%

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Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Ilyina,

Patrusheva,

Goltsova

et al. 2024

J. Org. Chem.

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Chiral oxygen-containing heterocyclic compounds are of great interest for the development of pharmaceuticals. Monoterpenes and their derivatives are naturally abundant precursors of novel synthetic chiral oxygencontaining heterocyclic compounds. In this study, acid catalyzed reactions of salicylic aldehydes with (−)-8-acetoxy-6-hydroxymethyllimonene, readily accessible from α-pinene, leads to the formation of chiral polycyclic products of various structural types. Three of the six isolated chiral heterocyclic products obtained from salicylic aldehyde contain previously unknown polycyclic ring types. Having carried out the reaction in the presence of Brønsted or Lewis acids (Amberlyst 15, trifluoromethanesulfonic acid, trifluoroacetic acid and boron trifluoride etherate) or aluminosilicates (montmorillonite K10, halloysite nanotubes), we found that the nature of products depends on the catalyst as well as the reaction conditions (reaction time, reactant ratio, presence or absence of solvent). Detailed mechanistic insight on the complex cascade reactions for product formation is provided with extensive experimental and quantum mechanical computational studies.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Ilyina,

Patrusheva,

Goltsova

et al. 2024

J. Org. Chem.

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Catalytic synthesis of heterocyclic compounds with a cineole moiety based on α-pinene

Sidorenko,

Khalimonyuk,

Kurban

et al. 2025

Applied Catalysis A: General

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Halloysite Clay Nanotubes for Catalytic Conversion of Biomass: Synergy between Computational Modeling and Experimental Studies

Lisuzzo,

Guercio,

Cavallaro

et al. 2024

ACS Catal.

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Halloysite clay nanotubes (HNTs) are emerging nanomaterials for numerous environmental applications, including catalysis and biomass valorization. The efficacy of halloysite as a nanoplatform for the catalytic conversion of biomass can be accurately evaluated by combined approaches based on experimental investigations and computational modeling. Recently, many efforts have been made to properly describe the most peculiar features of halloysite by focusing on its structural and interfacial features through computational studies, which are challenging for natural clay nanoparticles yet crucial for the design of novel catalysts to be exploited in biomass conversion. Within this framework, this review critically and extensively discusses recent advancements related to the use of halloysite in different catalytic processes, such as enzymatic reactions, preciousand nonprecious-metal-and alloy-catalyzed reactions, and acid-activated mechanisms. The research gap on the computational modeling of biomass chemical conversion occurring on halloysite surfaces is highlighted throughout this review, together with the latest experimental achievements. To optimize the catalytic efficiency of halloysite-based materials for biomass valorization, future efforts should focus on the implementation of experimental data with calculations provided by proper models in a synergistic approach.

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Catalytic condensation of α-pinene with formaldehyde

Cited by 6 publications

References 52 publications

Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

Catalytic synthesis of heterocyclic compounds with a cineole moiety based on α-pinene

Halloysite Clay Nanotubes for Catalytic Conversion of Biomass: Synergy between Computational Modeling and Experimental Studies

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