Heterocycles

Regio-and stereoselective addition of nucleophiles to 1-phenoxycarbonyl-2, 3-dihydropyridinium salts

DL Comins, G Chung, MA Foley

Index: Comins, Daniel L.; Chung, Geewon; Foley, Michael, A. Heterocycles, 1994 , vol. 37, # 2 p. 1121 - 1140

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Citation Number: 34

Abstract

Résumé/Abstract Several 2-alkyl-1-phenoxycarbonyl-Δ 3-piperidines were prepared by the addition of alkylzinc iodides to dihydropyridinium salt (9). The treatment of 4-hydroxy-2- methyl-1-phenoxycarbonyl-1, 2, 3, 4-tetrahydro-pyridine (12) with allyltrimethylsilane in the presence of a variety of Lewis acids was studied and found to give cis-and trans-2-6-dialkyl- Δ 3-piperidines (14) and (15) in moderate to good yield. Among the Lewis acids studied, ...