Addition of diethyl 2-bromomesaconate to N-tosylpiperidone enamine

✍ Scribed by A.W.J.D. Dekkers; W.N. Speckamp; H.O. Huisman

• Book ID: 104247404
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 209 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)96476-7

✦ Synopsis

As potential precursors in the synthesis of functionalized l-azaadamantanes, the substituted 3-aza-bicycle-[3,3,1]nonanes 1 are of considerable interest. A convenient preparation for the latter type 4 of compound is the addition of a-bromomethacrylates to ensmine 2. Recent work in the cyclohexanone series5 comprises both mechanistic aspects of the addition and conformational investigations about some adducts of the bicycle-[3,3,l]nonane type. The observation of novel mechanistic as well as conformational aspects in the piperidone series prompts us to disclose some of our results. As described esrlier4, the addition of acrylate 2 (2, R=H) to enamine