Rearrangement of beta-amino alcohols via aziridiniums: a review.
This tutorial review focuses on the rearrangement of beta-amino alcohols via aziridinium intermediates. It covers the literature from 1947 to January 2009 (55 references). The rearrangement of beta-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 R(2) substituent. In some cases, solvent as well as temperature can influence the ratio of amines.
Métro
Thomas-Xavier
TX
Laboratoire de Chimie Organique, Ecole Supérieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI ParisTech), CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Duthion
Béranger
B
Gomez Pardo
Domingo
D
Cossy
Janine
J