3,7-disubstituted bicyclo [3.3.1] nonanes—II : Synthesis and conformation of some 3,7-disubstituted 9-oxobicyclo [3.3.1] nonanes |
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| Authors: | J.A. Peters J.M. van der Toorn H. van Bekkum |
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| Affiliation: | Laboratory of Organic Chemistry, Delft University of Technology, Julianalaan 136, Delft, The Netherlands |
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| Abstract: | ![]()
Condensation of pyrrolidine enamines of 4-alkylcyclohexanones with methyl α-(bromomethyl)acrylate affords methyl 7β- and 7α-alkyl-9-oxobicyclo [3.3.1] nonane-3α-carboxylates in a ratio of 3:2. The mechanism of the annelation reaction is discussed. The conformations of the reaction products and their epimers have been studied by means of PMR spectroscopy. |
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