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.

中文翻译：

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2-Alken-4-olides的对映选择性合成和感官特性

一系列光学活性的C 2链烯-4- olides的₆ -C ₁₁与由甲基（的Sharpless不对称二羟基化（AD）89-97％对映体过量（ee）的值，获得ë）-3-链烯酸酯，接着通过甲磺酸盐消除。对映异构体的气味特征和阈值通过手性气相色谱-嗅觉（GC-O）测定。数据显示，所有样品在感觉特性上均表现出立体特异性差异。2辛烯4醇的对映体的两个气味阈值最低，而2烯丙基4烯醇的两个对映体的气味阈值最高。