Solid-phase tandem radical addition-cyclization reaction: triethylborane-induced reaction of oxime ethers anchored to polymer support

Chem Pharm Bull (Tokyo). 2004 Jul;52(7):842-7. doi: 10.1248/cpb.52.842.

Abstract

Tandem radical addition-cyclization of oxime ethers anchored to polymer support was studied. The reaction of oxime ethers with stannyl radical proceeded effectively by the use of triethylborane as a radical initiator. The alkyl radical addition-cyclization reactions of oxime ether connected with alpha,beta-unsaturated carbonyl group proceeded under iodine atom-transfer reaction conditions to give the functionalized azacycles via two carbon-carbon bonds-forming process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemistry
  • Boranes / metabolism*
  • Ethers / chemistry
  • Ethers / metabolism*
  • Free Radicals / chemistry
  • Free Radicals / metabolism*
  • Oximes / chemistry
  • Oximes / metabolism*
  • Polymers / chemistry
  • Polymers / metabolism*

Substances

  • Boranes
  • Ethers
  • Free Radicals
  • Oximes
  • Polymers
  • triethylborane