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Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides

Abstract

A series of optically active 2‐alken‐4‐olides of C6‐C11 were obtained with 89–97% enantiomeric excess (ee) values by the Sharpless asymmetric dihydroxylation (AD) of methyl (E)‐3‐alkenoates, followed by elimination via mesylates. The odor features and thresholds of the enantiomers were determined by means of chiral gas chromatography‐olfactory (GC‐O). The data revealed that all the samples exhibited stereospecific differences in sensory properties. Both enantiomers of 2‐octen‐4‐olide had the two lowest odour thresholds, whereas two enantiomers of 2‐undecen‐4‐olide presented the two highest odour thresholds.

A series of optically active 2‐alken‐4‐olides of C6‐C11 were obtained with 89‐97% enantiomeric excess (ee) values by the Sharpless asymmetric dihydroxylation (AD) of methyl (E)‐3‐alkenoates, followed by elimination via mesylates. The odor features and thresholds of the enantiomers were determined by means of chiral gas chromatography‐olfactory (GC‐O). The data revealed that all the samples exhibited stereospecific differences in sensory properties. Both enantiomers of 2‐octen‐4‐olide had the two lowest odor thresholds, whereas two enantiomers of 2‐undecen‐4‐olide presented the two highest odor thresholds.

Authors:   Yifeng Dai, Yongguo Liu, Baoguo Sun, Shaoxiang Yang, Hongyu Tian
Journal:   Flavour and Fragrance Journal
Year:   2017
Pages:   n/a
DOI:   10.1002/ffj.3415
Publication date:   07-Sep-2017
Facts, background information, dossiers
  • Elimination
  • Dihydroxylation
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