Hongyu Tian, Hong Ye, Baoguo Sun
Nov 1, 2011
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0
Influential Citations
7
Citations
Journal
Flavour and Fragrance Journal
Abstract
Enantioselective syntheses of two stereoisomers of 3-hydroxy-4-phenyl-2-butanone were investigated via Shi's asymmetric epoxidation or Sharpless asymmetric dihydroxylation of silyl enol ether. (R)-3-Hydroxy-4-phenyl-2-butanone was obtained in 73% enantiomeric excess (ee) by Shi's catalyst/oxone and 80% ee by AD-mix-β, while the (S)-isomer was prepared in 62% ee by AD-mix-α. The characteristic odour of the optically active products was analysed by gas chromatography–olfactometry. The (R)-isomer had a relatively weak fruity and green odour, while the (S)-isomer had a strong caramel, sweet and floral aroma. Additionally, the (S)-isomer presented a stronger odour intensity than did the (R)-isomer. Copyright © 2011 John Wiley & Sons, Ltd.