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

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...

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Bibliographic Details
Published in:Chemical Society reviews 2010-02, Vol.39 (2), p.783-816
Main Authors: Alcaide, Benito, Almendros, Pedro, Aragoncillo, Cristina
Format: Article
Language:English
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Summary: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).
ISSN:0306-0012
1460-4744
DOI:10.1039/b913749a