Three-Component Cycloadditions: The First Transition Metal-Catalyzed [5+2+1] Cycloaddition Reactions

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• 作者：Paul A. Wender ; Gabriel G. Gamber ; Robert D. Hubbard ; and Lei Zhang
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：March 27, 2002
• 年：2002
• 卷：124
• 期：12
• 页码：2876 - 2877
• 全文大小：38K
• 年卷期：v.124,no.12(March 27, 2002)
• ISSN：1520-5126

文摘

Prompted by our studies of transition metal-catalyzed [4+4], [4+2], [5+2], and [6+2] cycloadditions and by the view that these two-component reactions could be intercepted by a third component of one or more atoms, a new three-component transition metal-catalyzed cycloaddition is described. This new [5+2+1] cycloaddition proceeds in good to excellent yield and with high or complete regioselectivity with a variety of carbonyl-substituted alkynes to give bicyclo[3.3.0]octenone adducts, resulting from transannular closure of the intermediate eight-membered-ring cycloadduct. Effects of concentration, temperature, pressure, and catalyst loading on the efficiency of the reaction are discussed. This process provides access to complex building blocks for synthesis based on simple, readily available components.