Palladium-Catalyzed Dearomative Trimethylenemethane Cycloaddition Reactions

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• 作者：Barry M. Trost ; Veronika Ehmke ; B. Michael O鈥橩eefe ; Dustin A. Bringley
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：June 11, 2014
• 年：2014
• 卷：136
• 期：23
• 页码：8213-8216
• 全文大小：235K
• 年卷期：v.136,no.23(June 11, 2014)
• ISSN：1520-5126

文摘

A general protocol for the palladium-catalyzed dearomative trimethylenemethane [3+2] cycloaddition reaction with simple nitroarene substrates is described. This methodology leads to the exclusive formation of the dearomatized alicyclic products without subsequent rearomatization. The reaction is tolerant toward a broad range of heterocyclic and benzenoid substrates. The use of chiral bisdiamidophosphite ligands enabled the development of an enantioselective variant of this transformation, representing one of the rare examples of an asymmetric catalytic dearomatization process.