Synthesis of 5-Substituted 7,8-Benzomorphans by Intramolecular Cyclization of N-Protected 4,4-Disubstituted 1,4-Dihydropyridines

[摘要]：An efficient and high yielding method for the synthesis of 7,8-benzomorphans with varying substituents at C5 has been developed. It is based on an acid-catalyzed intramolecular cyclization reaction of N-protected 4,4-disubstituted 1,4-dihydropyridines, which are easily accessible by the addition of diorganomagnesium compounds to N-silylpyridinium ions. The cyclization reaction proceeds via N-acyliminium ions generated from the 1,4-dihydropyridine moiety that undergo electrophilic aromatic substitution reaction at the benzyl substituent present at C4 of the 1,4-dihydropyridine ring system.

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