2021Asian Journal of Organic ChemistryRequires access

A Formal [3+3+1] Reaction of Enyne‐Methylenecyclopropanes through Au(I)‐Catalyzed Enyne Cycloisomerization and Rh(I)‐Catalyzed [6+1] Reaction of Vinylspiropentanes and CO

Chen‐Long Li, Yusheng Yang, Yi Zhou, Zhi‐Xiang Yu

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Abstract

Abstract A formal [3+3+1] reaction through gold(I)‐catalyzed enyne cycloisomerization of enyne‐methylenecyclopropanes and rhodium(I)‐catalyzed [6+1] reaction of vinylspiropentanes and CO has been developed to synthesize aza‐6/7 bicyclic compounds, hexahydrocyclohepta[ c ]pyridinones. DFT calculations reveal that four steps are involved in the [6+1] cycloaddition of vinylspiropentanes and CO, including oxidative addition of cyclopropane to Rh, β−C elimination, CO insertion and reductive elimination.

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Abstract A formal [3+3+1] reaction through gold(I)‐catalyzed enyne cycloisomerization of enyne‐methylenecyclopropanes and rhodium(I)‐catalyzed [6+1] reaction of vinylspiropentanes and CO has been developed to synthesize aza‐6/7 bicyclic compounds, hexahydrocyclohepta[ c ]pyridinones. DFT calculations reveal that four steps are involved in the [6+1] cycloaddition of vinylspiropentanes and CO, including oxidative addition of cyclopropane to Rh, β−C elimination, CO insertion and reductive elimination.

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Available abstract

Abstract A formal [3+3+1] reaction through gold(I)‐catalyzed enyne cycloisomerization of enyne‐methylenecyclopropanes and rhodium(I)‐catalyzed [6+1] reaction of vinylspiropentanes and CO has been developed to synthesize aza‐6/7 bicyclic compounds, hexahydrocyclohepta[ c ]pyridinones. DFT calculations reveal that four steps are involved in the [6+1] cycloaddition of vinylspiropentanes and CO, including oxidative addition of cyclopropane to Rh, β−C elimination, CO insertion and reductive elimination.

Key concepts: Cycloisomerization, Enyne, Chemistry, Cycloaddition, Catalysis, Rhodium, Cyclopropane, Bicyclic molecule

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A Formal [3+3+1] Reaction of Enyne‐Methylenecyclopropanes through Au(I)‐Catalyzed Enyne Cycloisomerization and Rh(I)‐Catalyzed [6+1] Reaction of Vinylspiropentanes and CO — Research Paper | ScholarLens