Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 7, Pages 1561-1568Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588666
Keywords
pheromones; biocatalysis; chiral resolution; enzymes; 2-hydroxy 3-ketones; enantioselectivity
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Funding
- MINECO [AGL2012-39869-C02-01]
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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.
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