Gold Catalyzed Cyclopropanation/[5+3] Cycloaddition of 1,4,9‐ and 1,4,10‐Allenenynes to Bicyclo[3.3.1]nonane Derivatives

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-03, Vol.362 (5), p.1084-1095
Main Authors: Chen, Xianxiao, Zhou, Yuanyuan, Jin, Jianwen, Farshadfar, Kaveh, Ariafard, Alireza, Rao, Weidong, Chan, Philip Wai Hong
Format: Article
Language:English
Subjects:
carbocyclic synthesis
cyclization
gold
homogenous catalysis
synthetic methods
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901263