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Tandem nucleophilic addition-cycloaddition of arynes with α-iminoesters: two concurrent pathways to imidazolidines
Hao Jia1, Zhenyan Guo, Honglei Liu
1College of Science, China Agricultural University, Beijing 100193, China. hchguo@cau.edu.cn.
Abstract:
The tandem nucleophilic addition-cycloaddition reaction has been developed for the synthesis of functionalized imidazolidine derivatives. A variety of α-iminoesters and aryne precursors were well tolerated under the mild reaction conditions. This asymmetric cycloaddition afforded imidazolidine derivatives with high yields, complete regioselectivities, and excellent diastereo- and enantioselectivities. Aryne-induced ylides working as 1,3-dipoles for asymmetric cycloaddition are the notable feature of the present reaction. In the tandem reaction, the [3+2] cycloaddition of aryne-induced ylides with metallized α-iminoesters and metal-catalyzed [3+2] cycloaddition of azomethine ylide with α-iminoesters are two concurrent pathways to imidazolidines.
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