Diasteroselective synthesis of new spiropiperidine scaffolds from the CN(R,S) building block

J Org Chem. 2005 May 27;70(11):4474-7. doi: 10.1021/jo050258d.

Abstract

A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.

MeSH terms

  • Alkaloids / chemistry
  • Chemistry, Organic / methods
  • Lithium / chemistry
  • Molecular Mimicry
  • Molecular Structure
  • Nitriles / chemistry*
  • Piperidines / chemical synthesis*
  • Stereoisomerism
  • Thermodynamics

Substances

  • Alkaloids
  • Nitriles
  • Piperidines
  • Lithium