Synthesis of Longhorn Beetle Pheromone Components by Proline-Mediated α-Hydroxylation of Alkyl Ketones

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 - organocatalysis

Publication History

Received: 14 June 2021

Accepted after revision: 30 June 2021

Accepted Manuscript online:
30 June 2021

Article published online:
05 August 2021

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