An Organocatalyzed enantioselective synthesis of (2S,3R,4S)-4-hydroxyisoleucine and its stereoisomers

J Org Chem. 2010 Apr 16;75(8):2745-7. doi: 10.1021/jo100233u.


A concise enantioselective total synthesis of (2S,3R,4S)-4-hydroxyisoleucine and its stereoisomers is described. A key feature of this protocol is a catalytic enantioselective mannich reaction that is either anti- or syn-selective as genesis of chirality.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Isoleucine / analogs & derivatives*
  • Isoleucine / chemical synthesis
  • Isoleucine / chemistry
  • Kinetics
  • Stereoisomerism
  • Substrate Specificity


  • Isoleucine
  • (2S,3S,4R)-gamma-hydroxyisoleucine