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)
Preview |
Text.
Filename: Alamillo_Ferrer_etal_OL_2016_Alkene_dioxygenation_with_malonoyl_peroxides.pdf
Accepted Author Manuscript Download (1MB)| Preview |
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.
-
-
Item type: Article ID code: 56646 Dates: DateEvent17 June 2016Published17 June 2016Published Online12 June 2016AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 13 Jun 2016 14:15 Last modified: 29 Jul 2024 01:53 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/56646
CORE (COnnecting REpositories)