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Aryne‐Induced Novel Tandem 1,2‐Addition/(3+2) Cycloaddition to Generate Imidazolidines and Pyrrolidines
Author(s) -
Swain Sharada P.,
Shih YiChun,
Tsay ShwuChen,
Jacob Joby,
Lin ChunCheng,
Hwang Kuo Chu,
Horng JiaCherng,
Hwu Jih Ru
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503319
Subject(s) - aryne , cycloaddition , chemistry , intramolecular force , alkene , stereoselectivity , tandem , methylene , azomethine ylide , ring (chemistry) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , 1,3 dipolar cycloaddition , catalysis , materials science , composite material
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.