Ruthenium-catalyzed cycloisomerizations of diynols.
Ruthenium-catalyzed cycloisomerizations of diynols.
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DOI：
10.1021/ja043097o
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发表时间：
2005-03
影响因子：
15
通讯作者：
B. Trost;M. Rudd
中科院分区：
文献类型：
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作者：
B. Trost;M. Rudd
多种含有叔、仲和伯炔醇的二炔醇在催化量的 [CpRu(CH(3)CN)(3)]PF(6) 存在下发生环异构化反应，形成二烯酮和二烯醛。使用这种方法可以形成五元环和六元环。仲二炔醇反应形成单一几何异构体二烯酮和二烯酮。伯二炔醇经历环异构化以及水合环化过程。伯二炔醇环异构化的效用在 (+)-α-红藻氨酸的合成中得到了证明。
A wide variety of diynols containing tertiary, secondary, and primary propargylic alcohols undergo a cycloisomerization reaction to form dienones and dienals in the presence of a catalytic amount of [CpRu(CH(3)CN)(3)]PF(6). The formation of five- and six-membered rings is possible using this methodology. Secondary diynols react to form single geometrical isomeric dienones and -als. Primary diynols undergo a cycloisomerization as well as a hydrative cyclization process. The utility of primary diynol cycloisomerization is demonstrated in a synthesis of (+)-alpha-kainic acid.