Aryne‐Induced Novel Tandem 1, 2‐Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines1. (3rd July 2015)

• Record Type: Journal Article
• Authors: Swain, Sharada P.; Shih, Yi‐Chun; Tsay, Shwu‐Chen; Jacob, Joby; Lin, Chun‐Cheng; Hwang, Kuo Chu; Horng, Jia‐Cherng; Hwu, Jih Ru
• Is Part Of: Angewandte Chemie. Volume 127:Number 34(2015)
• Page Start: 10064
• Page End: 10068
• Publication Date: 2015-07-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201503319
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new "single‐flask" method was developed for the synthesis of imidazolidines and pyrrolidines with high stereoselectivity. First, a Schiff base was arylated with an aryne. Second, an intramolecular proton transfer took place from the methylene position to the anionic aryne ring. Third, the resultant ylide reacted with a second equivalent of the same Schiff base in situ or an electron‐deficient alkene through a (3+2) cycloaddition. These sequential tandem 1, 2‐addition/(3+2) cycloaddition reactions led to the desired heterocycles in 63–88 % yields.</p> </abstract>