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Synlett 1994; 1994(6): 451-453
DOI: 10.1055/s-1994-22887
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Zirconocene-Mediated Synthesis of 3,4-Disubstituted Piperidines and Reduced Isoquinolines

Mark I. Kemp* , Richard J. Whitby, Steven J. Coote
  • *Department of Chemistry, The University, Southampton, SO9 5NH, England
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Publication Date:
18 September 2002 (online)

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4-Aza-1,7-octa-dienes, -enynes, -ynenes and -diynes are converted to 3-aza-8-zirconabicyclo[4.3.0]non-anes,-6-enes,9-enes or 6,9-dienes when treated with 'ZrCp2' (where Cp = η5-C5H5). Protonolysis, iodinolysis, or carbonylation of these complexes affords 3,4-disubstituted piperidines. 1,3-Dienes formed from the coupling / protonolysis of 4-aza-1,7-octadiynes react with activated dienophiles to yield reduced isoquinolines.