A synthetic method to prepare cycloalkyl‐ and (hetero)aryl‐fused bicyclo[3.3.1]nonane derivatives from gold(I)‐catalyzed cyclopropanation/[5+3] cycloaddition of 1,4,9‐ and 1,4,10‐allenenynes is described. The suggested double cycloisomerization mechanism delineates the first example of a stepwise [5+3] cycloaddition pathway in gold catalysis, a mode of reactivity that is also sparse in organic chemistry. Experimental and Density Functional Theory (DFT) computational studies based on a proposed gold carbenoid species provides insight into this unique selectivity that leads to the assembly of the architecturally challenging bridged carbocyclic motif.

中文翻译：

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金催化的1,4,9-和1,4,10-烯丙炔的环丙烷化/ [5 + 3]环化成双环[3.3.1]壬烷衍生物

一种合成方法，由金（I）催化的1,4,9-和1,4,10的环丙烷化/ [5 + 3]环加成反应制备环烷基和（杂）芳基稠合的双环[3.3.1]壬烷衍生物描述了烯丙炔。所提出的双环异构化机理描述了金催化中逐步[5 + 3]环加成途径的第一个例子，该反应在有机化学中也是稀疏的。基于拟议的金类类胡萝卜素的实验和密度泛函理论（DFT）计算研究提供了对这种独特选择性的洞察力，该选择性导致了具有建筑挑战性的桥连碳环基序的组装。