Alkene dioxygenation with malonoyl peroxides : synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans

Alamillo-Ferrer, Carla and Karabourniotis-Sotti, Marianna and Kennedy, Alan R. and Campbell, Matthew and Tomkinson, Nicholas C. O. (2016) Alkene dioxygenation with malonoyl peroxides : synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans. Organic Letters. ISSN 1523-7060

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    Abstract

    Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.