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|Title:||Novel route to functionalized cyclooctanoids via [5+3] cycloaddition|
Intramolecular 4+4 Cycloadditions
|Publisher:||AMER CHEMICAL SOC|
|Citation:||JOURNAL OF ORGANIC CHEMISTRY, 69(3), 967-969|
|Abstract:||The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclo-octanoids is described. Different functionalities were introduced on the dimer (3) and the stereochemical outcome was determined by single-crystal X-ray analysis. It is noteworthy that the hydrogenation of 3 in ethanol solvent gave the transannulated product 5, whereas the expected dihydro product 4 was obtained when the reaction was run in nonnucleophilic solvents. The mechanistic pathway is discussed.|
|Appears in Collections:||Article|
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