One-Pot Formation of Piperidine- and Pyrrolidine-Substituted Pyridinium Salts via Addition of 5-Alkylaminopenta-2,4-dienals to N-Acyliminium Ions: Application to the Synthesis of (+/-)-Nicotine and Analogs

[摘要]：Addition of 5-alkylaminopenta-2,4-dienals onto N-acyliminium ions, generated in situ from alpha-hydroxycarbamates derived from pyrrolidine or piperidine, in the presence of zinc triflate, followed by dehydrative cyclization, allowed the formation of pyridinium salts substituted at their 3-position by a five- or six-membered nitrogen heterocycle. Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (+/-)-nicotine and analogs.

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