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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/3979

Title: Novel route to functionalized cyclooctanoids via [5+3] cycloaddition
Authors: KRISHNA, UM
DEODHAR, KD
TRIVEDI, GK
MOBIN, SM
Keywords: ring-closing metathesis
intramolecular 4+4 cycloadditions
olefin metathesis
organic-synthesis
catalyzed cycloadditions
nitrogen-heterocycles
samarium(ii) iodide
dienes
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.
URI: http://dx.doi.org/10.1021/jo0353583
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3979
http://hdl.handle.net/10054/3979
ISSN: 0022-3263
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