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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
Author(s) -
Chen Xianxiao,
Zhou Yuanyuan,
Jin Jianwen,
Farshadfar Kaveh,
Ariafard Alireza,
Rao Weidong,
Chan Philip Wai Hong
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901263
Subject(s) - carbenoid , cycloaddition , chemistry , cyclopropanation , nonane , bicyclic molecule , cycloisomerization , catalysis , reactivity (psychology) , selectivity , aryl , density functional theory , computational chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , rhodium , medicine , alkyl , alternative medicine , pathology
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.