Novel route to functionalized cyclooctanoids via [5+3] cycloaddition.
The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclooctanoids 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.
Krishna
Urlam Murali
UM
Department of Chemistry, National Single-Crystal X-ray Diffraction Facility, Indian Institute of Technology Bombay, Mumbai 400076, India.
Deodhar
Kodand D
KD
Trivedi
Girish K
GK
Mobin
Shaikh M
SM