Vasil'ev A A, Vlasyuk A L, Gamalevich G D, Serebryakov E P
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation.
Bioorg Med Chem. 1996 Mar;4(3):389-400. doi: 10.1016/0968-0896(96)00016-8.
A combination of the Horner-Emmons synthesis of alkyl 2,4-dienoates with their hydrogenation over complex L.Cr(CO)3 catalysts (L = 3CO or arene) provides a versatile, stereocontrolled and operationally simple approach to the (Z)-disubstituted, (Z)-trisubstituted, (E)-trisubstituted alkenes and skipped (Z,Z)-disubstituted diolefins with a homoallylic type of functionally. This protocol, sometimes supplemented by an enzymatic hydrolysis, was successfully applied to the synthesis of configurationally pure (gp > or = 98%) pheromones of the furniture carpet beetle, dry bean beetle, rusty grain beetle, square-necked grain beetle and a trail-following pheromone mimic for subterranean termites.
将2,4 - 二烯酸烷基酯的霍纳 - 埃蒙斯合成法与它们在配合物L·Cr(CO)₃催化剂（L = 3CO或芳烃）上的氢化反应相结合，为合成具有烯丙基型官能团的(Z)-二取代、(Z)-三取代、(E)-三取代烯烃以及间隔的(Z,Z)-二取代二烯烃提供了一种通用、立体可控且操作简单的方法。该方案有时辅以酶促水解，已成功应用于合成构型纯（对映体过量≥98%）的家具地毯甲虫、干豆象、赤拟谷盗、方颈谷盗的信息素以及一种用于地下白蚁的追踪信息素类似物。
