title: Aryne-Induced Novel Tandem 1,2-Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines.
abstract: 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.
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).
authors.forename: Sharada P
authors.initials: SP
authors.lastname: Swain
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).
authors.forename: Yi-Chun
authors.initials: YC
authors.lastname: Shih
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).|Department of Chemistry, National Central University, Jhongli City 32001 (Taiwan).
authors.forename: Shwu-Chen
authors.initials: SC
authors.lastname: Tsay
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).
authors.forename: Joby
authors.initials: J
authors.lastname: Jacob
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).
authors.forename: Chun-Cheng
authors.initials: CC
authors.lastname: Lin
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).
authors.forename: Kuo Chu
authors.initials: KC
authors.lastname: Hwang
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan).
authors.forename: Jia-Cherng
authors.initials: JC
authors.lastname: Horng
authors.affiliation: Department of Chemistry and Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013 (Taiwan). jrhwu@mx.nthu.edu.tw.|Department of Chemistry, National Central University, Jhongli City 32001 (Taiwan). jrhwu@mx.nthu.edu.tw.
authors.forename: Jih Ru
authors.initials: JR
authors.lastname: Hwu
keywords: 1,3-dipolar cycloaddition; arynes; azomethine ylides; imidazolidines; pyrrolidines