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    Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones

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    Publication date
    2016-09
    Author
    Throup, Adam
    Patterson, Laurence H.
    Sheldrake, Helen M.
    Keyword
    Cyclobutanes; Thermal enamine; Diastereoselective intramolecular enamine; Lactone; Lactam; Cyclobutenes
    Rights
    © 2016 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
    Peer-Reviewed
    Yes
    
    Metadata
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    Abstract
    Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.
    URI
    http://hdl.handle.net/10454/9488
    Version
    published version paper
    Citation
    Throup A, Patterson LH and Sheldrake HM (2016) Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicylolactones. Organic and Biomolecular Chemistry. 40(14): 9554-9559.
    Link to publisher’s version
    http://dx.doi.org/10.1039/C6OB01661H
    Type
    Article
    Collections
    Life Sciences Publications

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