Iodocyclization of chiral CF3-allylmorpholinones: a versatile strategy for the synthesis of enantiopure alpha-Tfm-prolines and alpha-Tfm-dihydroxyprolines

Org Lett. 2009 Jan 1;11(1):209-12. doi: 10.1021/ol8024567.

Abstract

An efficient iodocyclization reaction of a chiral Tfm-allylmorpholinone provides a straightforward route to alpha-Tfm-prolines and alpha-Tfm-dihydroxyprolines. The methodologies developed are particularly well adapted for gram-scale synthesis of enantiopure compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Cyclization
  • Fluorocarbons / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Morpholines / chemistry*
  • Proline / analogs & derivatives*
  • Proline / chemical synthesis*
  • Proline / chemistry
  • Stereoisomerism

Substances

  • Fluorocarbons
  • Morpholines
  • Proline