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Synlett 1991; 1991(5): 351-352
DOI: 10.1055/s-1991-34724
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A Convenient Synthesis of 1,5-Dialkyl-1,2,3,4-tetrahydropyridines. Synthons for Alkaloid Synthesis

Christian Stevens* , Norbert De Kimpe
  • *Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure Links 653, B-9000 Gent, Belgium
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Publikationsdatum:
07. März 2002 (online)

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1,5-Dialkyl-1,2,3,4-tetrahydropyridines, which are useful building blocks for alkaloid synthesis, are easily accesible from novel δ-chloroaldimines (N-alkyl/N-cycloalkyl-5-chloro-2-methylpentanimines). The synthetic strategy involves a straightforward construction of the title heterocycles from simple aldehydes via imination to aldimines, α-alkylation with 1-bromo-3-chloropropane to afford δ-chloroaldimines and ring closure with sodium isopropoxide.