University of Tasmania

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Gold catalyzed cyclopropanation/[5+3] cycloaddition of 1,4,9- and 1,4,10-allenenynes to bicyclo[3.3.1]nonane derivatives

journal contribution
posted on 2023-05-20, 11:20 authored by Chen, X, Zhou, Y, Jin, J, Farshadfar, K, Alireza AriafardAlireza Ariafard, Rao, W, Chan, PWH
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.


Australian Research Council

University of Wollongong


Publication title

Advanced Synthesis and Catalysis






School of Natural Sciences


Wiley-V C H Verlag Gmbh

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