Preparation and characteristic odour of optically active 3-hydroxy-2-octanone (pages 393–396)
Yong-guo Liu, Kai Chen, Chen Li, Shuo Zhang, Haitao Chen, Hong-yu Tian and Bao-guo Sun
Article first published online: 27 JUL 2012 | DOI: 10.1002/ffj.3117
The preparation of optically active 3-hydroxy-2-octanone was examined by Sharpless asymmetric dihydroxylation of a silyl enol ether derived from 2-octanone. (R)-3-hydroxy-2-octanone was obtained in 68% yield and 87.8% ee when AD-mix-β was used as an oxidant, while the (S)-enantiomer was produced in 69% yield and 77.3% ee from AD-mix-α. The characteristic odour of the optically active products was evaluated by chiral GC-O. (R)-3-Hydroxy-2-octanone has a mushroom-like, fresh grass odour, while the (S)-enantiomer presents a mushroom-like, earthy note. They obviously differ in odour intensity.