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Enones of (+)‐ and (−)‐3‐pinanone: influence of chirality on flavour
Author(s) -
Buchbauer G.,
ShafiiTabatabai A.
Publication year - 2003
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.1247
Subject(s) - chemistry , enone , aldol condensation , aldehyde , ketone , chirality (physics) , bicyclic molecule , enantiomer , aldol reaction , stereochemistry , methyl ketone , organic chemistry , catalysis , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Starting with (+)‐ and (−)‐3‐pinanone [(+)‐ and (−)‐ 2 ], the enones 3–12 were prepared by aldol condensation with various aldehydes. Without isolating the corresponding β ‐hydroxy ketones, the target compounds 3–12 could be obtained in good to moderate yields directly from the starting bicyclic ketone. The odour properties 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 avour impression of the enone. However, the (+)‐enantiomers generally possess more agreeable odours than their antipodes. Copyright © 2003 John Wiley & Sons, Ltd.