Ruthenium-Catalyzed Reactions of 1-Cyclopropyl-2-propyn-1-ols with Anilines and Water via Allenylidene Intermediates: Selective Preparation of Tri- and Tetrasubstituted Conjugated Enynes

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• 作者：Yoshihiro Yamauchi ; Gen Onodera ; Ken Sakata ; Masahiro Yuki ; Yoshihiro Miyake ; Sakae Uemura ; Yoshiaki Nishibayashi
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：April 25, 2007
• 年：2007
• 卷：129
• 期：16
• 页码：5175 - 5179
• 全文大小：135K
• 年卷期：v.129,no.16(April 25, 2007)
• ISSN：1520-5126

文摘

Ruthenium-catalyzed efficient preparation of the conjugated enynes can be carried out in thereactions of 1-cyclopropyl-2-propyn-1-ols with nitrogen- and oxygen-centered nucleophiles such as anilinesand water in the presence of a catalytic amount of sulfur-bridged diruthenium complexes. The use of suchcomplexes as catalysts realizes the completely stereoselective preparation of tri- and tetrasubstitutedconjugated enynes, where ruthenium-allenylidene complexes work as key intermediates. The direct attackof nucleophiles on a cyclopropane ring connected to an allenylidene ligand is a key step to obtain theenynes stereoselectively.