A new route to methyl (R,E)-(-)-tetradeca-2,4,5-trienoate (pheromone of Acanthoscelides obtectus) utilizing a palladium-catalyzed asymmetric allene formation reaction

被引：61

作者：

Ogasawara, M ^{[1
]}

Nagano, T

Hayashi, T

机构：

[1] Hokkaido Univ, Ctr Catalysis Res, Kita Ku, Sapporo, Hokkaido 0010021, Japan

[2] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0010021, Japan

[3] Kyoto Univ, Dept Chem, Grad Sch Sci, Kyoto 6068502, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 14期

关键词：

D O I：

10.1021/jo050684z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal total synthesis of the sex attractant of male dried bean beetle, methyl (RE)-(-)-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.

引用

页码：5764 / 5767

页数：4

共 52 条

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