Sequential elimination-reduction reactions promoted by samarium diiodide: synthesis of 2,3-dideuterioesters or -amides

Chemistry. 2001 Oct 1;7(19):4266-71. doi: 10.1002/1521-3765(20011001)7:19<4266::aid-chem4266>3.0.co;2-8.

Abstract

A facile and general sequential elimination/reduction process promoted by samarium diiodide provides an efficient method for synthesizing saturated esters or amides 3 from readily available starting materials. The reaction involves a beta-elimination of the starting 2-halo-3-hydroxyesters or -amides 1 and subsequent 1,4-reduction of the obtained alpha,beta-unsaturated esters or amides in the presence of H2O. When D20 is used instead of H2O, 2,3-dideuterioesters or -amides 4 are isolated. A mechanism is proposed to account for this synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Deuterium / chemistry*
  • Esters / chemical synthesis*
  • Iodides / chemistry*
  • Isotope Labeling / methods*
  • Samarium / chemistry*

Substances

  • Amides
  • Esters
  • Iodides
  • Samarium
  • Deuterium
  • samarium diiodide