Selective synthesis of cyclooctanoids by radical cyclization of seven-membered lactones: neutron diffraction study of the stereoselective deuteration of a chiral organosamarium

Xavier Just-Baringo, Jemma Clark, Matthias Gutmann, David Procter

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Seven-membered lactones undergo selective SmI2–H2O-promoted radical cyclization to form substituted cyclooctanols. The products arise from an exo-mode of cyclization rather than the usual endo-attack employed in the few radical syntheses of cyclooctanes. The process is terminated by the quenching of a chiral benzylic samarium. A labeling experiment and neutron diffraction study have been used for the first time to probe the configuration and highly diastereoselective deuteration of a chiral organosamarium intermediate.
    Original languageEnglish
    JournalAngewandte Chemie - International Edition
    Volume55
    Issue number40
    Early online date7 Sep 2016
    DOIs
    Publication statusPublished - 19 Sep 2016

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