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Issue 6, 2012
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Allylic alcohols as synthetic enolate equivalents: Isomerisation and tandem reactions catalysed by transition metal complexes

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Abstract

Allylic alcohols can be isomerised into carbonyl compounds by transition metal complexes. In the last few years, catalyst design and development have resulted in highly efficient isomerisations under mild reaction conditions, including enantioselective versions. In addition, the isomerisation of allylic alcohols has been combined with C–C bond forming reactions when electrophiles such as aldehydes or imines were present in the reaction mixture. Also, C–F bonds can be formed when electrophilic fluorinating reagents are used. Thus, allylic alcohols can be treated as latent enol(ate)s. In this article, we highlight the latest developments concerning the isomerisation of allylic alcohols into carbonyl compounds, focusing in particular on tandem isomerisation/C–C or C–heteroatom bond formation processes. Significant attention is given to the mechanistic aspects of the reactions.

Graphical abstract: Allylic alcohols as synthetic enolate equivalents: Isomerisation and tandem reactions catalysed by transition metal complexes

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Article information


Submitted
05 Sep 2011
Accepted
04 Nov 2011
First published
03 Jan 2012

Dalton Trans., 2012,41, 1660-1670
Article type
Perspective

Allylic alcohols as synthetic enolate equivalents: Isomerisation and tandem reactions catalysed by transition metal complexes

N. Ahlsten, A. Bartoszewicz and B. Martín-Matute, Dalton Trans., 2012, 41, 1660
DOI: 10.1039/C1DT11678A

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