Rearrangement of β-amino alcohols via aziridiniums: a review

Abstract

This tutorial review focuses on the rearrangement of β-amino alcohols via aziridinium intermediates. It covers the literature from 1947 to January 2009 (55 references). The rearrangement of β-amino alcohols can be performed by activation of the hydroxy group followed by the addition of nucleophiles (Nu). In most examples, an aziridinium intermediate is involved in the rearrangement. The ratio of amines resulting from the attack of nucleophiles at either the C-1 or C-2 position of the aziridinium intermediate, depends on the nature of the nucleophiles and the R² substituent. In some cases, solvent as well as temperature can influence the ratio of amines.