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Issue 8, 2016
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Allenes, versatile unsaturated motifs in transition-metal-catalysed [2+2+2] cycloaddition reactions

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Abstract

The development of efficient reactions that enable the construction of multiple bonds and/or stereogenic centres in a single synthetic operation is of great interest for greener and step-economical syntheses of complex organic targets. Transition-metal-catalysed [2+2+2] cycloadditions excell in this regard: no fewer than three new sigma bonds and a new ring system are formed from simple unsaturated components. Allenes constitute an important subclass among these. They are more reactive than simple alkenes and generate sp3 centres, with important stereochemical implications. In addition, further manipulation of the resulting cycloadduct through the remaining double bond is possible, increasing molecular complexity. This tutorial review highlights the value that allenes have as reagents in [2+2+2] cycloaddition and their great versatility for the development of methods to generate complex architectures.

Graphical abstract: Allenes, versatile unsaturated motifs in transition-metal-catalysed [2+2+2] cycloaddition reactions

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Publication details

The article was received on 07 Jul 2015 and first published on 03 Feb 2016


Article type: Tutorial Review
DOI: 10.1039/C5CS00535C
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Chem. Soc. Rev., 2016,45, 2010-2023
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    Allenes, versatile unsaturated motifs in transition-metal-catalysed [2+2+2] cycloaddition reactions

    A. Lledó, A. Pla-Quintana and A. Roglans, Chem. Soc. Rev., 2016, 45, 2010
    DOI: 10.1039/C5CS00535C

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