Literature DB >> 12357722

Aziridines: epoxides' ugly cousins?

J B Sweeney1.   

Abstract

Aziridines, the nitrogenous analogues of epoxides, have until recently excited far less interest amongst synthetic organic chemists than their oxygenated counterparts, with some justification. A range of reviews concerned with the physical properties, synthesis (asymmetric and otherwise), reactions and utility of aziridines exists; this review briefly summarizes the similarities and differences between oxiranes and their nitrogenated analogues, concentrating on the underlying properties of aziridines and recent developments in their chemistry. In addition to descriptions of the physical nature of aziridines, especially those features which underpin their utility as synthetic intermediates, the sections beneath describe reactions involving alkylative ring-opening and synthesis of aziridines.

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Year:  2002        PMID: 12357722     DOI: 10.1039/b006015l

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  52 in total

1.  Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations.

Authors:  Minsoo Ju; Cale D Weatherly; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

2.  Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids.

Authors:  Zhiwei Ma; Zhe Zhou; László Kürti
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

3.  Arene C-H amination at nickel in terphenyl-diphosphine complexes with labile metal-arene interactions.

Authors:  David E Herbert; Nadia C Lara; Theodor Agapie
Journal:  Chemistry       Date:  2013-10-14       Impact factor: 5.236

4.  Styrene Aziridination by Iron(IV) Nitrides.

Authors:  Salvador B Muñoz; Wei-Tsung Lee; Diane A Dickie; Jeremiah J Scepaniak; Deepak Subedi; Maren Pink; Michael D Johnson; Jeremy M Smith
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-15       Impact factor: 15.336

5.  Three-coordinate terminal imidoiron(III) complexes: structure, spectroscopy, and mechanism of formation.

Authors:  Ryan E Cowley; Nathan J DeYonker; Nathan A Eckert; Thomas R Cundari; Serena DeBeer; Eckhard Bill; Xavier Ottenwaelder; Christine Flaschenriem; Patrick L Holland
Journal:  Inorg Chem       Date:  2010-07-05       Impact factor: 5.165

6.  Highly efficient synthesis of enantiomerically enriched 2-hydroxymethylaziridines by enzymatic desymmetrization.

Authors:  Jun Young Choi; Richard F Borch
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

7.  Stereoselective Synthesis of trans-Olefins by the Copper-Mediated S(N)2' Reaction of Vinyl Oxazines with Grignard Reagents. Asymmetric Synthesis of D-threo-Sphingosines.

Authors:  Om V Singh; Hyunsoo Han
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

8.  Effective synthesis of chiral N-fluoroaryl aziridines through enantioselective aziridination of alkenes with fluoroaryl azides.

Authors:  Li-Mei Jin; Xue Xu; Hongjian Lu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-15       Impact factor: 15.336

9.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

10.  Dearomatization reactions of aryl-substituted silaaziridines.

Authors:  Zulimar Nevárez; K A Woerpel
Journal:  J Org Chem       Date:  2008-09-03       Impact factor: 4.354

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