NMR evidence of the kinetic and thermodynamic products in the NIS promoted cyclization of 1-phenyl-4-pentenylamines. Synthesis and reactivity of trans-2-phenyl-5-iodopiperidines

Chem Commun (Camb). 2011 Mar 21;47(11):3251-3. doi: 10.1039/c0cc05105e. Epub 2011 Jan 28.

Abstract

The intramolecular reaction of secondary amines with tethered alkenes using NIS was studied, which gave insight into the kinetic vs. thermodynamic control of the iodoaminocyclization and the regioselectivity of the aziridinium ring-opening reactions, and led to functionalized piperidines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Amines / chemical synthesis
  • Amines / chemistry*
  • Cyclization
  • Deuterium / chemistry
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Thermodynamics

Substances

  • Alkenes
  • Amines
  • Piperidines
  • Deuterium