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 (https://doi.org/10.1021/acs.orglett.6b01253)

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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.

ORCID iDs

Alamillo-Ferrer, Carla ORCID logoORCID: https://orcid.org/0000-0003-3607-846X, Karabourniotis-Sotti, Marianna, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Campbell, Matthew ORCID logoORCID: https://orcid.org/0000-0002-6003-7257 and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
CORE (COnnecting REpositories)