Iridium complex-catalyzed reaction of 1,6-enynes: Cycloaddition and cycloisomerization

Iridium complex-catalyzed reaction of 1,6-enynes: Cycloaddition and cycloisomerization
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DOI:
10.1021/ol050085e
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发表时间:
2005-04-28
期刊:
影响因子:
5.2
通讯作者:
Takeuchi, R
Takeuchi, R
中科院分区:
化学1区
文献类型:
--
作者:
Kezuka, S;Okado, T;Takeuchi, R

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在催化量的[Ir(cod)Cl](2)/配体存在下,1,6-烯炔与单炔反应生成环己二烯衍生物. DPPE最适合环加成反应。非对映选择性环加成也是可能的。在不存在单炔的情况下,1,6-烯炔环异构化为(2)-1-亚烷基-2-亚甲基环戊烷衍生物。DPPF最适合环化反应。这些结果是高Z-选择性环化异构化的第一个例子。
1,6-Enynes reacted with monoynes to give cyclohexadiene derivatives in the presence of a catalytic amount of (Ir(cod)CI](2)/ligand. DPPE was most suitable for cycloaddition. Diastereoselective cycloaddition was also possible. In the absence of monoynes, 1,6-enynes cycloisomerized to (2)-1-alkylidene-2-methylenecyclopentane derivatives. DPPF was most suitable for cyclolsomerization. These results are the first examples of highly Z-selective cycloisomerization.