Nucleophilic Addition to 3-Substituted Pyridinium Salts: Expedient Syntheses of (−)-L-733,061 and (−)-CP-99,994
2004; American Chemical Society; Volume: 6; Issue: 20 Linguagem: Inglês
10.1021/ol048624n
ISSN1523-7060
AutoresAlexandre Lemire, M. Grenon, Mehrnaz Pourashraf, André B. Charette,
Tópico(s)Synthesis and Catalytic Reactions
ResumoThe addition of nucleophiles to 3-substituted pyridinium salts prepared from N-methylbenzamide and various pyridines has been investigated. Good to excellent regioselectivities favoring the 2,3-disubstituted 1,2-dihydropyridines were observed. The resulting 1,2-dihydropyridines led to the corresponding 2,3-disubstituted pyridines upon treatment with Mn(OAc)3/NaIO4. This methodology was also successfully applied to the enantioselective syntheses of (−)-L-733,061 and (−)-CP-99,994, two members of a new class of highly potent, nonpeptide, Substance P antagonists.
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