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DOI: 10.1055/a-1541-4939
Synthesis of Longhorn Beetle Pheromone Components by Proline-Mediated α-Hydroxylation of Alkyl Ketones
Programa de Desarrollo de Ciencias Básicas (PEDECIBA- PNUD/URU/06/004), Agencia Nacional de Investigación e Innovación (ANII).
Abstract
The stereoselective synthesis of several components of the aggregation pheromones of numerous longhorn beetle species is described. These attractants consist of 3-hydroxy-2-alkanones and 2,3-alkyldiols with chain lengths varying from six to ten carbons. The 3R- and 3S-series are generated by organocatalytic α-hydroxylation of alkyl ketones with nitrosobenzene in the presence of l- or d-proline, respectively, to obtain the hydroxyketones in high enantiomeric excess. Further reduction and chromatographic separation lead to the enantiomerically pure diols that complete the library.
Key words
(3R)-3-hydroxy-2-hexanone - (2R,3R)-2,3-hexanediol - aggregation pheromone - cerambycidae - organocatalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1541-4939.
- Supporting Information
Publikationsverlauf
Eingereicht: 14. Juni 2021
Angenommen nach Revision: 30. Juni 2021
Accepted Manuscript online:
30. Juni 2021
Artikel online veröffentlicht:
05. August 2021
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