SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations

Org Lett. 2003 Oct 30;5(22):4085-8. doi: 10.1021/ol0354831.

Abstract

[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Allyl Compounds / chemistry*
  • Amines / chemistry
  • Carbohydrates / chemistry
  • Catalysis
  • Ethers / chemistry*
  • Ethylamines / chemistry
  • Iodides / chemistry*
  • Molecular Structure
  • Phenyl Ethers / chemistry
  • Propylamines / chemistry
  • Samarium / chemistry*
  • Water / chemistry

Substances

  • Alcohols
  • Allyl Compounds
  • Amines
  • Carbohydrates
  • Ethers
  • Ethylamines
  • Iodides
  • Phenyl Ethers
  • Propylamines
  • Water
  • phenyl allyl ether
  • Samarium
  • samarium diiodide
  • 2-propylamine
  • triethylamine