March 1, 2003Journal of the American Chemical Society
Regio- and Enantioselective Iridium-Catalyzed Intermolecular Allylic Etherification of Achiral Allylic Carbonates with Phenoxides
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Discussion
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Implication
Experimental study demonstrates selective allylic etherification using an iridium catalyst, indicating an efficient catalytic route to construct chiral allylic aryl ethers.
Key Points
- To develop an enantioselective and regioselective intermolecular allylic etherification of achiral allylic carbonates using phenoxide nucleophiles.
- Coupled sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal aliphatic allylic electrophiles.
- Employed 2 mol % of an iridium-phosphoramidite catalyst complex in tetrahydrofuran solvent.
- Afforded chiral allylic aryl ethers in high chemical yields with high levels of regio- and enantioselectivity.
- Demonstrated broad scope across sterically hindered phenoxides, ortho-, meta-, and para-substituted aryloxides, and alkyl (E)-allylic carbonates.
Cite This Study
López et al. (2003) studied this question.