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Synlett 1998; 1998(1): 58-60
DOI: 10.1055/s-1998-1567
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1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis. Intramolecular Alkylation Reactions and Stereoselective Synthesis of Anti-2,6-Disubstituted Piperidines

Donald Craig* , Raymond McCague, Gerard A. Potter, Meredith R. V. Williams
  • *Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, U.K.; Fax +44 1 71-5 94-58 04; E-mail: dcraig@ic.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines 1 having R1 containing aromatic groups undergo intramolecular electrophilic aromatic substitution reactions to give benzo-fused bicyclo[3.3.1] systems with chemoselectivities which depend on the nature of the acidic reagent used. Cationic hydrogenation of the C-5-C-6 double bond in substrates 1 substituted at C-6 provides an entry to anti-2,6-disubstituted piperidines upon desulfonylation.

aziridine - sulfone - piperidine - cyclisation - SN1′