Acid-modified Halloysite Nanotubes as a Stereoselective Catalyst for Synthesis of 2H-Chromene Derivatives by the Reaction of Isopulegol with Aldehydes

AY Sidorenko, AV Kravtsova, Atte Aho, I Heinmaa, KP Volcho, NF Salakhutdinov, VE Agabekov, Dmitry Murzin

Tutkimustuotos: LehtiartikkeliArtikkeliTieteellinenvertaisarvioitu

13 Sitaatiot (Scopus)
3 Lataukset (Pure)

Abstrakti

Acid-modified halloysite nanotubes were used for the first time as a stereoselective catalyst for synthesis of oxygen-containing heterocycles applying of allyl alcohol (-)-isopulegol condensation with aldehydes to the octahydro-2H-chromenol (4R- and 4S-diastereomers) as an example. The catalysts were characterized by XRF, XRD, N-2-adsorption, FTIR with pyridine and MAS NMR methods. A high ratio of 4R/4S diastereomers (7.6-14.5) under mild conditions in cyclohexane was considerably exceeding previously reported results. Unprecedented selectivity (79-83%) to 4R isomer of thiophenyl-substituted chromenol exhibiting high analgesic activity was achieved. An increase in stereoselectivity with a decrease in the halloysite drying temperature and catalyst acidity clearly indicates formation of 4R diastereomer on the weak BrOnsted sites. This work is an example that control of the stereoselectivity of acid-catalyzed organic reactions can be effectively carried out by varying water content on the aluminosilicate surface. Modified halloysite nanotubes can be considered as extremely promising catalysts for stereoselective synthesis of heterocyclic compounds.
AlkuperäiskieliEi tiedossa
Sivut3950–3954
Sivumäärä5
JulkaisuChemCatChem
Vuosikerta10
Numero18
DOI - pysyväislinkit
TilaJulkaistu - 2018
OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

Keywords

  • halloysite
  • nanotubes
  • stereoselective catalysis
  • chromene

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