Literature DB >> 15548060

Synthesis of enantiopure imidazolines through a Ritter reaction of 2-(1-aminoalkyl)aziridines with nitriles.

José M Concellón1, Estela Riego, José Ramón Suárez, Santiago García-Granda, M Rosario Díaz.   

Abstract

The Ritter reaction of enantiopure 2-(1-aminoalkyl)aziridines 1 with different nitriles afford enantiopure tetrasubstituted imidazolines 2. The opening of the aziridine ring takes place with total regio- and stereoselectivity. A mechanism to explain the described addition reaction is proposed. [reaction: see text]

Entities:  

Year:  2004        PMID: 15548060     DOI: 10.1021/ol048176j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Azomethine ylide mediated inversion of configuration of quaternary imidazoline carbon: converting trans- to its cis- imidazolines.

Authors:  Ke Qu; Jason S Fisk; Jetze J Tepe
Journal:  Tetrahedron Lett       Date:  2011-09-21       Impact factor: 2.415

2.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

3.  Theoretical investigation of the regioselective ring opening of 2-methylaziridine. Lewis acid effect.

Authors:  Emna Cherni; Khaled Essalah; Néji Besbes; Manef Abderrabba; Sameh Ayadi
Journal:  J Mol Model       Date:  2018-10-09       Impact factor: 1.810

  3 in total

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