We describe in this work a short six-step convergent high-scale synthesis of the sex pheromone of the horse-chestnut leaf miner ((8E,10Z)-tetradeca-8,10-dienal). This procedure relies on a key stereoselective iron-catalyzed Kumada cross-coupling, which affords the coupling product in high yield in the absence of additional ligands or additives. DFT calculations moreover suggest that ω-alkoxide groups on iron-ligated chains in transient organoiron(II) intermediates can enhance their stability and hamper their decomposition in off-cycle β-hydride elimination reactions.

中文翻译：

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基于关键配体和无添加剂的铁催化交叉偶联，可快速，轻松地扩展马栗叶矿工（Cameraria ohridella）的性信息素的合成

我们在这项工作中描述了七叶树栗矿机（（8 E，10 Z）-tetradeca-8,10-dienal）的性信息素的短六步收敛高级合成。该方法依赖于关键的立体选择性铁催化的熊田交叉偶联，其在不存在其他配体或添加剂的情况下以高收率提供偶联产物。DFT计算还表明，在瞬态有机铁（II）中间体中，铁连接链上的ω-醇盐基团可以增强其稳定性并阻碍其在非循环β-氢化物消除反应中的分解。