4.7 Article

Straightforward Access to Enantioenriched 2-Allylpiperidine: Application to the Synthesis of Alkaloids

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 1, Pages 780-784

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo202211u

Keywords

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Funding

  1. Spanish Ministerio de Ciencia e Innovacion [CTQ2007-65218, 2010-CSD-2007-00006, CTQ2011-24165]
  2. Generalitat Valenciana [PROMETEO/2009/039]
  3. University of Alicante

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An efficient stereocontrolled preparation of (2R,R-S)-2-allyl-(N-tert-butylsulfinyl)piperidine and its enantiomer is detailed. The sequence requires only two synthetic operations with one-column chromatography and is readily scaled up. The versatility of these chiral building blocks was exemplified by the total or formal synthesis of some natural and unnatural alkaloids.

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