Literature DB >> 16575458

Regio- and stereospecific ring opening of 1,1-dialkyl-2-(aryloxymethyl)aziridinium salts by bromide.

Matthias D'hooghe1, Veronique Van Speybroeck, Michel Waroquier, Norbert De Kimpe.   

Abstract

Enantiomerically pure 2-(aryloxymethyl)aziridines are efficiently transformed into chiral N-(2-bromo-3-aryloxypropyl)amines via a regio- and stereospecific ring opening of the intermediate aziridinium salts, and the experimental results are rationalized on the basis of some high level ab initio calculations.

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Year:  2006        PMID: 16575458     DOI: 10.1039/b518298k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  4 in total

1.  Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles.

Authors:  Nagendra Nath Yadav; Hyun-Joon Ha
Journal:  J Vis Exp       Date:  2018-08-22       Impact factor: 1.355

Review 2.  Strained Ammonium Precursors for Radiofluorinations.

Authors:  Falco Reissig; Constantin Mamat
Journal:  ChemistryOpen       Date:  2022-06       Impact factor: 2.630

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

4.  Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride.

Authors:  Christina Schjoeth-Eskesen; Paul Robert Hansen; Andreas Kjaer; Nic Gillings
Journal:  ChemistryOpen       Date:  2014-11-21       Impact factor: 2.911

  4 in total

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