Highly Stereoselective Generation of Complex Oxy-Bicyclic Scaffolds via an Atom-Economic Pd(II)-Catalyzed Hydroalkynylation, Isomerization and Diels–Alder Cycloaddition Sequence

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• 作者：Ruwei Shen ; Ke Chen ; Qiulin Deng ; Jianjun Yang ; Lixiong Zhang
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 21, 2014
• 年：2014
• 卷：16
• 期：4
• 页码：1208-1211
• 全文大小：347K
• ISSN：1523-7052

文摘

An atom-economic tandem Pd(II)-catalyzed hydroalkynylation, alkyne-allene isomerization, and Diels鈥揂lder cycloaddition is reported. The reaction employs readily available starting substrates, proceeds in a highly ordered fashion, features high regio- and stereoselectivity, and tolerates a wide range of functionality and structural motifs, thus offering an attractive strategy for producing new molecular complexity and diversity from easily available starting materials. A mechanistic study with density functional theoretical calculations was conducted to rationalize the observed stereoselectivity.