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Synthesis 2017; 49(07): 1561-1568
DOI: 10.1055/s-0036-1588666
DOI: 10.1055/s-0036-1588666
paper
New and Convenient Chemoenzymatic Syntheses of (S)-2-Hydroxy-3-octanone, the Major Pheromone Component of Xylotrechus spp., and Its R-Enantiomer
Further Information
Publication History
Received: 14 October 2016
Accepted after revision: 11 November 2016
Publication Date:
15 December 2016 (online)
Abstract
New and efficient chemoenzymatic approaches for the synthesis of both enantiomers of 2-hydroxy-3-octanone in good yields and excellent enantioselectivity are presented. The S-enantiomer is a pheromone component of economically important pests in Japan, India, China, and other Asian countries. The enzymatic approaches involve transesterification of the racemic acyloin with vinyl acetate in the presence of Candida antarctica lipase B (CAL B) in 99% ee of both enantiomers (E = 167–618), or hydrolysis of the acetylated acyloin by double kinetic resolution with CAL B and C. antarctica lipase A (CAL A) in 96–98% ee of either enantiomer (E = 458). CAL A and CAL B induce reverse enantioselectivity.
Key words
pheromones - biocatalysis - chiral resolution - enzymes - 2-hydroxy 3-ketones - enantioselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588666 and contains experimental details for the intermediates in the synthesis of acyloin (±)-1 and copies of the 1H and 13C NMR spectra for new compounds and intermediates.
- Supporting Information
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