Org. Lett., 8 (7), 1419 -1422, 2006. 10.1021/ol060197l S1523-7060(06)00197-0
Web Release Date: March 7, 2006

Copyright © 2006 American Chemical Society

Sequential Pd- and Rh-Catalyzed Three-Component Cyclization with Allenylboronate Platform

Keisuke Tonogaki, Kenichiro Itami,* and Jun-ichi Yoshida*

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, and Research Center for Materials Science, Nagoya University, Nagoya 464-8602, Japan

itami@chem.nagoya-u.ac.jp; yoshida@sbchem.kyoto-u.ac.jp

Received January 24, 2006

Abstract:

A novel three-component cyclization using allenylboronate ester is described. A three-component assembly of allenylboronate ester, aryl iodides, and stabilized carbon nucleophiles took place in the presence of palladium catalyst, furnishing functionalized alkenylboronate esters with high regio- and stereoselectivity. A Rh-catalyzed cyclization of the resultant three-component products then afforded interesting carbocyclic frameworks efficiently.


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