Tandem nucleophilic addition–cycloaddition of arynes with α-iminoesters: two concurrent pathways to imidazolidines. Issue 51 (7th June 2018)

• Record Type: Journal Article
• Authors: Jia, Hao; Guo, Zhenyan; Liu, Honglei; Mao, Biming; Shi, Xueyan; Guo, Hongchao
• Is Part Of: Chemical communications. Volume 54:Issue 51(2018)
• Page Start: 7050
• Page End: 7053
• Publication Date: 2018-06-07
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc03806f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The tandem nucleophilic addition-cycloaddition reaction of arynes with α-iminoesters gave functionalized imidazolidine derivatives with high yields, complete regioselectivities, and excellent diastereo- and enantioselectivities. 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.