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Novel route to functionalized cyclooctanoids via [5+3] cycloaddition

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Title Novel route to functionalized cyclooctanoids via [5+3] cycloaddition
 
Creator KRISHNA, UM
DEODHAR, KD
TRIVEDI, GK
MOBIN, SM
 
Subject ring-closing metathesis
intramolecular 4+4 cycloadditions
olefin metathesis
organic-synthesis
catalyzed cycloadditions
nitrogen-heterocycles
samarium(ii) iodide
dienes
 
Description 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.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T14:17:56Z
2011-12-26T12:48:25Z
2011-12-27T05:37:53Z
2011-07-14T14:17:56Z
2011-12-26T12:48:25Z
2011-12-27T05:37:53Z
2004
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 69(3), 967-969
0022-3263
http://dx.doi.org/10.1021/jo0353583
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3979
http://hdl.handle.net/10054/3979
 
Language en