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Allylic alcohols as synthetic enolate equivalents: Isomerisation and tandem reactions catalysed by transition metal complexes
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-7898-317X
2012 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 41, no 6, 1660-1670 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2012. Vol. 41, no 6, 1660-1670 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-76742DOI: 10.1039/c1dt11678aISI: 000299292400002OAI: oai:DiVA.org:su-76742DiVA: diva2:527209
Funder
Swedish Research CouncilKnut and Alice Wallenberg FoundationVINNOVAKnut and Alice Wallenberg FoundationBerzelii Centre EXSELENT
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Available from: 2012-05-18 Created: 2012-05-16 Last updated: 2017-11-10Bibliographically approved

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