J. Am. Chem. Soc., 128 (10), 3130 -3131, 2006. 10.1021/ja060291x S0002-7863(06)00291-5
Web Release Date: February 15, 2006

Copyright © 2006 American Chemical Society

Pd(II)-Catalyzed Enantioselective Oxidative Tandem Cyclization Reactions. Synthesis of Indolines through C-N and C-C Bond Formation

Kai-Tai Yip, Min Yang, Ka-Lun Law, Nian-Yong Zhu, and Dan Yang*

Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China

yangdan@hku.hk

Received January 15, 2006

Abstract:

We have developed an efficient Pd(II)-catalyzed enantioselective oxidative tandem cyclization strategy using molecular oxygen as a green oxidant for the double 5-exo-trig cyclizations of N-(2-allylaryl) amides to afford a variety of indolines in good yields without the formation of undesired monocyclization products. By employing Pd(TFA)2/(-)-sparteine as the chiral catalyst, we obtained tandem cyclization products with high enantioselectivity (up to 91% ee).

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