Oligometallic template strategy for ring-closing olefin metathesis: highly cis- and trans-selective synthesis of a 32-membered macrocyclic tetraoxime

被引:58
|
作者
Akine, Shigehisa [1 ]
Kagiyama, Satoko [1 ]
Nabeshima, Tatsuya [1 ]
机构
[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan
关键词
D O I
10.1021/ic701585x
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An oligometallic template effect was observed on the cis/trans selectivity of a 32-membered macrocyclic tetraoxime in ring-closing olefin metathesis of an acyclic diallyl derivative H4L; the metathesis of heterotrinuclear complex LZn2M (M = Ca2+, La3+) afforded the cis isomer, whereas uncomplexed H4L gave the trans isomer.
引用
收藏
页码:9525 / 9527
页数:3
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  • [4] The synthesis of highly functionalized seven-membered allyl ethers using palladium-catalyzed alkoxyallylation of activated olefins and ring-closing olefin metathesis
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    Goto, A
    Sato, D
    Kawai, H
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  • [6] Total synthesis of (-)-(7S,10R)-calamenene and (-)-(7S,10R)-2-hydroxycalamenene by use of a ring-closing metathesis reaction.: A comparison of the cis- and trans-isomers
    Nakashima, K
    Imoto, M
    Sono, M
    Tori, M
    Nagashima, F
    Asakawa, Y
    [J]. MOLECULES, 2002, 7 (07) : 517 - 527