Microwave-Assisted Palladium(0)-Catalyzed Alkylative Cyclization of Allenyl Aldehydes Leading to 3-Substituted 3-Cycloalken-1-ols
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- 作者：Hirokazu Tsukamoto ; Tomotaka Matsumoto ; Yoshinori Kondo
- 刊名：Journal of the American Chemical Society
- 出版年：2008
- 出版时间：January 16, 2008
- 年：2008
- 卷：130
- 期：2
- 页码：388 - 389
- 全文大小：63K
- 年卷期：v.130,no.2(January 16, 2008)
- ISSN：1520-5126
文摘
We have developed an efficient synthetic method for 3-substituted 3-cyclohexenols and -cyclopentenol based on Pd0-catalyzed alkylative, arylative, alkenylative, alkynylative, and borative cyclization reaction of allene-carbonyl compounds. Microwave irradiation increases not only the reaction rate but also the product yield by suppressing formation of hydroarylation byproducts observed in the same catalytic system. Cyclization of optically active 1,3-disubstituted allene aldehyde reveals that the reaction proceeds not through carbopalladation but through "anti-Wacker"-type oxidative addition.