Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives

J Am Chem Soc. 2006 Aug 9;128(31):10002-3. doi: 10.1021/ja063115x.

Abstract

Protected homoallylic amines are synthesized by the decarboxylative coupling of alpha-amino acid derivatives. The catalytic C-C bond-forming reaction relies on the bioinspired decarboxylative metalation of alpha-amino acids to produce alpha-amino anion equivalents. The alpha-amino anion equivalents are intercepted by pi-allyl palladium electrophiles to produce substituted homoallylic amines.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amines / chemical synthesis*
  • Amino Acids / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Palladium / chemistry*

Substances

  • Amines
  • Amino Acids
  • Carboxylic Acids
  • Palladium