Concise syntheses of insect pheromones using Z-selective cross metathesis.

Concise syntheses of insect pheromones using Z-selective cross metathesis.
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DOI:
10.1002/anie.201206079
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发表时间:
2013-01-02
影响因子:
16.6
通讯作者:
Grubbs, Robert H.
Grubbs, Robert H.
中科院分区:
化学1区
文献类型:
--
作者:
Herbert, Myles B.;Marx, Vanessa M.;Pederson, Richard L.;Grubbs, Robert H.

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报道了合成含有多种功能的九种顺式信息素的最短途径,包括非共轭(E,Z)二烯。这些鳞翅目信息素被广泛用于害虫防治,并且很容易用基于钌的z -选择性交叉复分解制备,突出了这种方法比低效率的方法形成z -烯烃的优势。在实验过程中发现了对z选择性复分解机制的重要见解,并随后进行了探索。
The shortest synthetic routes to nine cis-pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported. These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z-olefins. Important insight into the mechanism of Z-selective metathesis was uncovered during experimentation and subsequently explored.
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