4.8 Article

One-Pot Asymmetric Synthesis of Substituted Piperidines by Exocyclic Chirality Induction

Journal

ORGANIC LETTERS
Volume 11, Issue 11, Pages 2333-2336

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900708d

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Funding

  1. WV Nano Initiative at West Virginia University
  2. American Chemical Society PRF

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A highly efficient one-pot synthesis of substituted piperidines was developed through nitroalkene, amine, and enone condensation. The transformation was suitable for a large group of substrates, giving excellent yields and diastereoselectivity. Reactions using chiral amines revealed a chirality induction through the unusual exocyclic stereochemistry control, producing enantiomeric pure piperidines in simple steps.

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