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Issue 1, 2010
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Rearrangement of β-amino alcohols via aziridiniums: a review

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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.

Graphical abstract: Rearrangement of β-amino alcohols via aziridiniums: a review

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Article information


Submitted
06 Oct 2008
First published
08 Sep 2009

Chem. Soc. Rev., 2010,39, 89-102
Article type
Tutorial Review

Rearrangement of β-amino alcohols via aziridiniums: a review

T. Métro, B. Duthion, D. Gomez Pardo and J. Cossy, Chem. Soc. Rev., 2010, 39, 89
DOI: 10.1039/B806985A

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