Organocatalysis by an aprotic imidazolium zwitterion: regioselective ring-opening of aziridines and applicable to gram scale synthesis / Ghosal Nirnita Chakraborty,Santra Sougata,Das Sudarshan,Hajra Alakananda,Zyryanov Grigory V.,Majee Adinath // GREEN CHEMISTRY. - 2016. - V. 18, l. 2. - P. 565-574.

ISSN/EISSN:

1463-9262 / 1463-9270

Type:

Article

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.

Author keywords:

TEMPERATURE IONIC LIQUIDS; SILYLATED NUCLEOPHILES; N-TOSYLAZIRIDINES; MESO-AZIRIDINES; ENANTIOSELECTIVE DESYMMETRIZATION; NONACTIVATED AZIRIDINES; VERSATILE CATALYSTS; CHIRAL AZIRIDINES; ORGANIC-REACTIONS; HIGHLY EFFICIENT

DOI:

10.1039/c5gc01323b

Web of Science ID:

ISI:000369534500030

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
EISSN	1463-9270
Keywords-Plus	TEMPERATURE IONIC LIQUIDS; SILYLATED NUCLEOPHILES; N-TOSYLAZIRIDINES; MESO-AZIRIDINES; ENANTIOSELECTIVE DESYMMETRIZATION; NONACTIVATED AZIRIDINES; VERSATILE CATALYSTS; CHIRAL AZIRIDINES; ORGANIC-REACTIONS; HIGHLY EFFICIENT
Research-Areas	Chemistry; Science \& Technology - Other Topics
Web-of-Science-Categories	Chemistry, Multidisciplinary; GREEN \& SUSTAINABLE SCIENCE \& TECHNOLOGY
Author-Email	adinath.majee@visva-bharati.ac.in
Funding-Acknowledgement	BRNS-DAE, Govt. of India {[}37(2)/14/35/2014-BRNS/563]; Russian Scientific Foundation {[}15-13-10033]
Funding-Text	A. Majee and N. Chakraborty are pleased to acknowledge financial support from BRNS-DAE, Govt. of India (Grant No. 37(2)/14/35/2014-BRNS/563). We are thankful to DST-FIST and UGC-SAP. S. Santra and G. V. Zyryanov acknowledge the Russian Scientific Foundation (ref. \# 15-13-10033) for funding.
Number-of-Cited-References	77
Usage-Count-Last-180-days	4
Usage-Count-Since-2013	26
Journal-ISO	Green Chem.
Doc-Delivery-Number	DC9IJ