Synthesis of Functionalised Piperidines Through a [3 + 3] Cycloaddition Strategy

Hedley, Simon J., Moran, Wesley J., Prenzel, Alexander H. G. P., Price, David A. and Harrity, Joseph P. A. (2001) Synthesis of Functionalised Piperidines Through a [3 + 3] Cycloaddition Strategy. Synlett (10). pp. 1596-1598. ISSN 09365214

Abstract

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.

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