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Synlett 1994; 1994(2): 110-112
DOI: 10.1055/s-1994-22757
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Convergent Synthesis of Aminobicyclo[3.3.0]octenes Using Zirconium Chemistry An Unusual Anti-1,3-Amine Shift.

Jeremy M. Davis* , Richard J. Whitby, Albert Jaxa-Chamiec
  • *Chemistry Department, The University, Southampton, SO9 5NH, England.
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Publication Date:
22 March 2002 (online)

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Insertion of phenyl isocyanide into zirconacyclopentenes affords iminoacyl complexes which rearrange to give α,β-unsaturated zirconocene η2-imine complexes. These insert alkenes or alkynes to afford elaborated cyclopentenylamines on protic work-up.The products undergo a facile anti-1,3-amine-shift to afford 1-anilinobicyclo[3.3.0]oct-2-enes.