An Unusual Samarium Diiodide Mediated Reductive Ring Contraction of a Tricyclic Oxazine to a Highly-Functionalized Cyclopentane and Cyclobutane
Organic Letters2000Vol. 2(10), pp. 1457–1459
Citations Over Time
Abstract
[reaction--see text] Samarium diiodide mediated reductive ring contraction of a substituted tricyclo[2.2.2]oxazine at 25 degrees C leads to a mixture of cyclopentane and cyclobutane rearrangement products with complete diastereoselectivity in each case. At -78 degrees C, the anticipated amidocyclohexanol reduction product is obtained exclusively, while the cyclopentane is the sole product at reflux in THF.
Related Papers
- → Group 15 biradicals: synthesis and reactivity of cyclobutane-1,3-diyl and cyclopentane-1,3-diyl analogues(2018)59 cited
- → Reduction of Multiple Bonds without Hydrogen or Hydride Complexes: Samarium Diiodide as a Mild Reducing Reagent(2006)19 cited
- → Novel and Efficient Cyanofluoromethylation Promoted by Samarium(II) Species(2007)5 cited
- → Anomaly in the ring strain behaviour of cyclopropane, cyclobutane, and cyclopentane, compared with their silicon analogues; a theoretical study(1985)16 cited
- → A Novel Stereospecific Aminocyclopropanation via the Dethiolation of Thioamides Promoted by the Samarium/Samarium Diiodide Mixed Reagent.(2005)