Regioselectivity in the ring opening of non-activated aziridines

In this critical review, the ring opening of non-activated 2-substituted aziridines via intermediate aziridinium salts will be dealt with. Emphasis will be put on the relationship between the observed regioselectivity and inherent structural features such as the nature of the C2 aziridine substituen...

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Veröffentlicht in:Chemical Society reviews Jg. 41; H. 2; S. 643
Hauptverfasser: Stanković, Sonja, D'hooghe, Matthias, Catak, Saron, Eum, Heesung, Waroquier, Michel, Van Speybroeck, Veronique, De Kimpe, Norbert, Ha, Hyun-Joon
Format: Journal Article
Sprache:Englisch
Veröffentlicht: England 21.01.2012
Schlagworte:
Alkylation
Aziridines - chemistry
Lewis Acids - chemistry
Protons
Stereoisomerism
ISSN:1460-4744, 1460-4744
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Zusammenfassung:In this critical review, the ring opening of non-activated 2-substituted aziridines via intermediate aziridinium salts will be dealt with. Emphasis will be put on the relationship between the observed regioselectivity and inherent structural features such as the nature of the C2 aziridine substituent and the nature of the electrophile and the nucleophile. This overview should allow chemists to gain insight into the factors governing the regioselectivity in aziridinium ring openings (81 references).
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ISSN:1460-4744
1460-4744
DOI:10.1039/c1cs15140a