%0 Journal Article %A Miller, Yan %A Miao, Lei %A Hosseini, Azade S. %A Chemler, Sherry R. %D 2012 %T Copper-Catalyzed Intramolecular Alkene Carboetherification: Synthesis of Fused-Ring and Bridged-Ring Tetrahydrofurans %U https://acs.figshare.com/articles/journal_contribution/Copper_Catalyzed_Intramolecular_Alkene_Carboetherification_Synthesis_of_Fused_Ring_and_Bridged_Ring_Tetrahydrofurans/2502064 %R 10.1021/ja3034075.s003 %2 https://ndownloader.figshare.com/files/4144990 %K aryl ring %K alkene addition step %K enantioselective reactions %K intramolecular %K Catalytic enantioselective alkene carboetherification reactions %K enantioselective process %K mechanism %K unactivated alkenes %K future development %K bicyclic tetrahydrofurans %K Mechanistic studies %K alkene hydroetherification %X Fused-ring and bridged-ring tetrahydrofuran scaffolds are found in a number of natural products and biologically active compounds. A new copper-catalyzed intramolecular carboetherification of alkenes for the synthesis of bicyclic tetrahydrofurans is reported herein. The reaction involves Cu-catalyzed intramolecular addition of alcohols to unactivated alkenes and subsequent aryl C–H functionalization provides the C–C bond. Mechanistic studies indicate a primary carbon radical intermediate is involved and radical addition to the aryl ring is the likely C–C bond-forming mechanism. Preliminary catalytic enantioselective reactions are promising (up to 75% ee) and provide evidence that copper is involved in the alkene addition step, likely through a cis-oxycupration mechanism. Catalytic enantioselective alkene carboetherification reactions are rare and future development of this new method into a highly enantioselective process is promising. During the course of the mechanistic studies a protocol for alkene hydroetherification was also developed. %I ACS Publications