Synfacts 2013; 9(5): 0503
DOI: 10.1055/s-0033-1338391
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aminoindanes via a Novel C−H Activation–[3+2]-Annulation Strategy

Contributor(s):
Mark Lautens
,
David A. Petrone
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
Further Information

Publication History

Publication Date:
17 April 2013 (online)

 

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.


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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.


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