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Diastereoselective one-pot synthesis of tetrafunctionalized 2-imidazolines.

Authors :
Janssen GV
Slobbe P
Mooijman M
Kruithof A
Ehlers AW
Guerra CF
Bickelhaupt FM
Slootweg JC
Ruijter E
Lammertsma K
Orru RV
Source :
The Journal of organic chemistry [J Org Chem] 2014 Jun 06; Vol. 79 (11), pp. 5219-26. Date of Electronic Publication: 2014 May 22.
Publication Year :
2014

Abstract

A convenient trans-selective one-pot synthesis of tetrafunctionalized 2-imidazolines is described. Our approach to these valuable heterocyclic scaffolds involves a formal 1,3-dipolar cycloaddition between nitrile ylides or nitrilium triflates and imines. A detailed experimental study in combination with a high-level computational exploration of reaction routes reveals a plausible reaction pathway that accounts for the observed diastereoselectivity.

Details

Language :
English
ISSN :
1520-6904
Volume :
79
Issue :
11
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
24820129
Full Text :
https://doi.org/10.1021/jo500790n