Nishimura T, * Ebe Y, Hayashi T. Kyoto University, Japan and National University of Singapore, Singapore
Iridium-Catalyzed [3+2] Annulation of Cyclic
N-Sulfonyl Ketimines with 1,3-Dienes via C–H Activation.
J. Am. Chem. Soc. 2013;
135: 2092-2095
Key words
iridium - [3+2] annulation - C−H activation
Significance
Directed ortho C–H functionalization has become a hot topic in organic synthesis in recent years. A novel extension is reported by Nishimura and co-workers, who accomplished an iridium-catalyzed annulation of N-sulfonyl ketimines with 1,3-dienes to provide complex aminoindane derivatives.
Comment
This transformation tolerates a wide variety of 1,3-diene substrates, and products are afforded in good to excellent yields and high regio- and stereoselectivity. Key to the proposed mechanism is the intramolecular aryl–iridium–π-allyl intermediate D.
