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Synfacts 2007(1): 0059-0059
DOI: 10.1055/s-2006-955738
DOI: 10.1055/s-2006-955738
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Cu(I)-Catalyzed Stereoselective Formation of Tertiary Alkyl-Aryl Ethers
P. Li, E. M. Forbeck, C. D. Evans, M. M. Joullié*
University of Pennsylvania, Philadelphia, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
15. Dezember 2006 (online)
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.