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- W2015681970 abstract "3-Azabicyclic Ketones from 1,3-Dialkoxy-2-azapropenylium Salts and Enamines of Cyclic Ketones1,3-Diethoxy-2-azapropenylium salts 1 are powerful biselectrophiles and react diastereoselectively with enamines of five-membered ring ketones 2 to yield novel 3-azabicyclo[3.2.1]oct-2-en-8-one 5 after hydrolysis of the intermediate iminium salts 3, 4. Some of the iminium salts 3 can be hydrolyzed further to provide the diketo imines 6. With enamines of six-membered ring ketones 7 the 3-azabicyclo[3.3.1]non-2-en-9-ones 10, 11 are obtained after hydrolytic workup. Mixtures of diastereomers 10/11 are found in the case of 7a, b, whereas with 7g — j the endo-phenyl derivatives 10 are formed exclusively. With the unsymmetrical enamine 7b only one regioisomer is observed. The decalone enamine 12 reacts with 1a to yield the tricyclic iminium salt 13. — The configuration of the bicyclic products has been determined by using NMR spectroscopic techniques (COSY, polarisation transfer by long range couplings); an X-;Ray analysis of compound 10a is used as basis for the NMR assignments. General rules for the determination of the stereochemistry of these azabicyclic systems by 1H-NMR shift arguments are derived." @default.
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- W2015681970 date "1993-01-01" @default.
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- W2015681970 title "3-Azabicyclische Ketone durch Reaktionen von 1,3-Diethoxy-2-azapropenylium-Salzen mit Enaminen cyclischer Ketone" @default.
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- W2015681970 doi "https://doi.org/10.1002/cber.19931260121" @default.
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