Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4574
Title: Chair-boat equilibrium as driving force in epimerization of 3,7-dimethylbicyclo[3.3.1]nonan-2,9-dione derivatives. Stereocontrolled synthesis of 3-exo,7-exo- and 3-endo,7-exo-3,7-dimethylbicyclo[3.3.1]nonan-9-ones
Authors: A., Gambacorta
D., Tofani
Tafi, Andrea 
M., ELMI FARAH
Issue Date: 2001
Project: None 
Journal: TETRAHEDRON
Abstract: 
Molecular mechanics calculations and experimental 1H NMR data are in close agreement and show that the epimerization equilibrium at C3 of 3,7-dimethylbicyclo[3.3.1]nonan-2,9-diones is shifted toward the 3-endo-epimer in order to reach the lowest energy chair-boat conformation. Introduction of a 1,3-dioxolane moiety at C9 results in reversal of the equilibrium, in protic solvents, leading mainly to the 3-exo-epimer in the most stable chair-chair conformation. These results have been applied to the stereocontrolled synthesis of the title compounds.
Description: 
19385
URI: http://hdl.handle.net/20.500.12779/4574
ISSN: 0040-4020
DOI: 10.1016/S0040-4020(01)00445-8
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