Cu(I)-Catalyzed Stereoselective Formation of Tertiary Alkyl-Aryl Ethers

Significance

A method was reported to effect the ring opening on propargyl aziridines via substitution by phenol nucleophiles. The challenging reaction, especially with trisubstituted aziridines, was regioselective and yielded the most substituted aryl-alkyl ethers. The reaction proceeded with complete inversion of stereochemistry as a single diastereomer was observed. Although the yields were modest, the compatibility of the reaction was demonstrated with the higly functionalized coupling partner 4. This constitutes the first report of a nucleophilic substitution occuring at the propargylic position.