Alpha-amidation of cyclic ethers catalyzed by simple copper salt and a mild and efficient preparation method for alpha,omega-amino alcohols

Org Lett. 2007 Jun 7;9(12):2277-80. doi: 10.1021/ol070537i. Epub 2007 May 11.

Abstract

Copper(II) trifluoromethanesulfonate catalyzed the amidation of cyclic ethers with iminoiodanes under mild conditions (CH2Cl2, 40 degrees C) with good yields (up to 86% based on 97% conversion) and selectivity (only alpha-amino products were found). Subsequently, the tosylamidated products could undergo a reductive ring-opening reaction to give alpha,omega-amino alcohols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry
  • Catalysis
  • Ethers, Cyclic / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amides
  • Amino Alcohols
  • Ethers, Cyclic
  • Organometallic Compounds
  • copper(II) trifluoromethanesulfonate