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|Title: ||Novel route to functionalized cyclooctanoids via [5+3] cycloaddition|
|Authors: ||KRISHNA, UM|
|Keywords: ||ring-closing metathesis|
intramolecular 4+4 cycloadditions
|Issue Date: ||2004|
|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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