A one pot synthesis of 3-azabicyclo3.3.1nonane-6,9-diones is described via the addition of acryloyl chloride to enamines of N-carboxy-4-piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclc system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo3.3.1nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).
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