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

Research output: Contribution to journalArticle

  • Authors:
  • Xavier Just-Baringo
  • Jemma Clark
  • Matthias Gutmann
  • David Procter

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.

Bibliographical metadata

Original languageEnglish
JournalAngewandte Chemie - International Edition
Volume55
Issue number40
Early online date7 Sep 2016
DOIs
StatePublished - 19 Sep 2016