One-step microwave-assisted asymmetric cyclisation/hydrogenation of citronellal to menthols using supported nanoparticles on mesoporous materials

The selective conversion of citronellal to menthols, with good diastereoselectivities to (-)-menthol for the case of (+)-citronellal as starting material, can effectively be carried out in a one-step reaction under microwave irradiation catalysed by supported nanoparticles on mesoporous materials. 2...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-06, Vol.8 (12), p.2845-2849
Main Authors: Balu, Alina Mariana, Campelo, Juan Manuel, Luque, Rafael, Romero, Antonio Angel
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Cyclization
Hydrogenation
Menthol - chemistry
Microwaves
Monoterpenes - chemistry
Nanoparticles - chemistry
Stereoisomerism
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Summary:The selective conversion of citronellal to menthols, with good diastereoselectivities to (-)-menthol for the case of (+)-citronellal as starting material, can effectively be carried out in a one-step reaction under microwave irradiation catalysed by supported nanoparticles on mesoporous materials. 2% Pt/Ga-MCM-41 was found to be the optimum catalyst for the reaction, with a quantitative conversion of starting material and selectivities above 85% to menthols obtained in short reaction times (typically 15 min). These results constitute the first report of a simple microwave-assisted one-step cyclisation/hydrogenation process for the production of menthols.
ISSN:1477-0520
1477-0539
DOI:10.1039/c003600e