Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: synthesis of cyclic amines with a tertiary fluorine at C3

J Org Chem. 2012 Jul 20;77(14):6087-99. doi: 10.1021/jo300887u. Epub 2012 Jul 2.

Abstract

As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of the ring expansion of cyclic 2-hydroxymethyl amines induced by diethylaminosulfur trifluoride (DAST) to produce cyclic β-fluoro amines was studied as well as the enantioselectivity of the process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Amino Alcohols / chemistry*
  • Cyclization
  • Diethylamines / chemistry*
  • Fluorine / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amines
  • Amino Alcohols
  • Diethylamines
  • Fluorine
  • diethylaminosulfur trifluoride