An unusual samarium diiodide mediated reductive ring contraction of a tricyclic oxazine to a highly-functionalized cyclopentane and cyclobutane.
[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.
McAuley
B J
BJ
School of Chemistry, The Queen's University of Belfast, 5AG, UK.
Nieuwenhuyzen
M
M
Sheldrake
G N
GN
D003503:Cyclobutanes / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007454:Iodides; D008958:Models, Molecular; D008968:Molecular Conformation; D010078:Oxazines / Q000737:chemistry*; D016958:Pseudomonas putida / Q000201:enzymology; D012493:Samarium
D003503:Cyclobutanes; D003517:Cyclopentanes; D007202:Indicators and Reagents; D007454:Iodides; D010078:Oxazines; D012493:Samarium; C409809:samarium diiodide