Premium
Synthesis and characteristic odour of optically active 3‐hydroxy‐4‐phenyl‐2‐butanone
Author(s) -
Tian Hongyu,
Ye Honglin,
Sun Baoguo,
Liu YuPing,
Huang Mingquan,
Chen Haitao
Publication year - 2011
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.2058
Subject(s) - chemistry , enantioselective synthesis , butanone , dihydroxylation , enantiomer , aroma , sharpless asymmetric dihydroxylation , optically active , enol , stereochemistry , organic chemistry , catalysis , food science , solvent
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.