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Issue 2, 2010
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Exploiting [2+2] cycloaddition chemistry: achievements with allenes

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Abstract

The allene moiety represents an excellent partner for the [2+2] cycloaddition with alkenes and alkynes, affording the cyclobutane and cyclobutene skeletons in a single step. This strategy has been widely studied under thermal, photochemical and microwave induced conditions. More recently, the use of transition metal catalysis has been introduced as an alternative relying on the activation of the allenic component. On the other hand, the intramolecular version has attracted much attention as a strategy for the synthesis of polycyclic compounds in a regio- and stereoselective fashion. This critical review focuses on the most recently developed [2+2] cycloadditions on allenes along with remarkable early works accounting for the mechanism, the regio- and diastereoselectivity of the cycloadducts formed (103 references).

Graphical abstract: Exploiting [2+2] cycloaddition chemistry: achievements with allenes

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Publication details

The article was received on 09 Jul 2009 and first published on 22 Oct 2009


Article type: Critical Review
DOI: 10.1039/B913749A
Chem. Soc. Rev., 2010,39, 783-816

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    Exploiting [2+2] cycloaddition chemistry: achievements with allenes

    B. Alcaide, P. Almendros and C. Aragoncillo, Chem. Soc. Rev., 2010, 39, 783
    DOI: 10.1039/B913749A

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