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Synthesis and characteristic odour of optically active 3-hydroxy-4-phenyl-2-butanone

✍ Scribed by Hong-yu Tian; Hong-lin Ye; Bao-guo Sun; Yu-Ping Liu; Ming-quan Huang; Hai-tao Chen

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
160 KB
Volume
26
Category
Article
ISSN
0882-5734

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✦ Synopsis

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.

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