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Organocatalysis by an aprotic imidazolium zwitterion: regioselective ring-opening of aziridines and applicable to gram scale synthesis

Author:
Chakraborty Ghosal, Nirnita, Santra, Sougata, Das, Sudarshan, Hajra, Alakananda, Zyryanov, Grigory V., Majee, Adinath
Source:
Green chemistry 2016 v.18 no.2 pp. 565-574
ISSN:
1463-9270
Subject:
Lewis bases, acetic acid, butanes, ethanol, ethyleneimine, green chemistry, indoles, methanol, organocatalysts, pyrroles, regioselectivity, sulfonates, zwitterions
Abstract:
An imidazole-based zwitterionic-salt, 4-(3-methylimidazolium)butane sulfonate (MBS), has been found to be an efficient organocatalyst for aziridine ring-opening regioselectively by various nucleophiles like indoles, pyrroles, methanol, ethanol, acetic acid and di-iso-propylamine. The reactions are highly regioselective and they always afford the products resulting from benzylic attack. The present methodology is applicable to gram scale synthesis.
Agid:
6397915