A new route to methyl (R,E)-(-)-tetradeca-2,4,5-trienoate (pheromone of Acanthoscelides obtectus) utilizing a palladium-catalyzed asymmetric allene formation reaction.
A new route to methyl (R,E)-(-)-tetradeca-2,4,5-trienoate (pheromone of Acanthoscelides obtectus) utilizing a palladium-catalyzed asymmetric allene formation reaction.
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DOI：
10.1021/jo050684z
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发表时间：
2005-06
期刊：
影响因子：
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通讯作者：
M. Ogasawara;T. Nagano;Tamio Hayashi
中科院分区：
文献类型：
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作者：
M. Ogasawara;T. Nagano;Tamio Hayashi
[反应：见正文] 利用 Pd 催化的不对称丙二烯合成反应，通过一种新的有效路线，正式全合成了雄性干豆甲虫的性引诱剂 (R,E)-(-)-tetradeca-2,4,5-trienoate。研究发现，在Pd催化制备烷基取代的轴向手性丙二烯的反应中，阻转异构联芳基双膦(R)-segphos表现出比(R)-binap更好的对映选择性。
[reaction: see text] A formal total synthesis of the sex attractant of male dried bean beetle, methyl (R,E)-(-)-tetradeca-2,4,5-trienoate, was achieved by a new efficient route utilizing the Pd-catalyzed asymmetric allene synthesis reaction. It was found that the atropisomeric biaryl bisphosphine (R)-segphos showed better enantioselectivity than (R)-binap in the Pd-catalyzed reaction for preparing alkyl-substituted axially chiral allenes.