Regioselectivity in the ring opening of non-activated aziridines

Chem Soc Rev. 2012 Jan 21;41(2):643-65. doi: 10.1039/c1cs15140a. Epub 2011 Sep 6.

Abstract

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).

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Alkylation
  • Aziridines / chemistry*
  • Lewis Acids / chemistry
  • Protons
  • Stereoisomerism

Substances

  • Aziridines
  • Lewis Acids
  • Protons