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Synlett 2001; 2001(10): 1596-1598
DOI: 10.1055/s-2001-17443
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Synthesis of Functionalised Piperidines Through a [3 + 3] Cycloaddition Strategy

Simon J. Hedley* , Wesley J. Moran, Alexander H. G. P. Prenzel, David A. Price, Joseph P. A. Harrity
  • *Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK; Fax + 44(114)2 73 86 73; E-mail: j.harrity@sheffield.ac.uk
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Publication Date:
27 September 2001 (online)

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A novel approach to functionalised piperidines is described through a [3 + 3] cycloaddition reaction of aziridines with Pd-trimethylenemethane complexes. Importantly, the employment of enantiomerically pure aziridines (prepared in three steps from the appropriate amino acids) allows the corresponding piperidines to be furnished in enantiomerically pure form. Additionally, the application of this technique in the total synthesis of (-)-pseudoconhydrine is described.

cycloadditions - aziridines - piperidines - palladium-trimethylenemethane