Enones of (+)- and (-)-3-pinanone: influence of chirality on flavour

Starting with (+)- and (-)-3-pinanone [(+)- and (-)-2], the enones 3-12 were prepared by aldol condensation with various aldehydes. Without isolating the corresponding beta-hydroxy ketones, the target compounds 3-12 could be obtained in good to moderate yields directly from the starting bicyclic ketone. The odour proper-ties of the enones were evaluated and described. It could be shown that the structure of the aldehyde as well as the chirality is crucial for the flavour impression of the enone. However, the (+)-enantiomers generally possess more agreeable odours than their antipodes. Copyright (C) 2003 John Wiley Sons, Ltd.