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

Xianxiao Chen, Yuanyuan Zhou, Jianwen Jin, Kaveh Farshadfar, Alireza Ariafard, Weidong Rao, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

Abstract

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. 

Original languageEnglish
Pages (from-to)1084-1095
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number5
DOIs
Publication statusPublished - 4 Mar 2020

Keywords

  • carbocyclic synthesis
  • cyclization
  • gold
  • homogenous catalysis
  • synthetic methods

Cite this