Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids

Angew Chem Int Ed Engl. 2015 Oct 26;54(44):12918-22. doi: 10.1002/anie.201507273. Epub 2015 Sep 14.

Abstract

Structurally simple and inexpensive chiral tridentate ligands were employed for substantially advancing the purely chemical dynamic kinetic resolution (DKR) of unprotected racemic tailor-made α-amino acids (TM-α-AAs), enabling the first DKR of TM-α-AAs bearing tertiary alkyl chains as well as multiple unprotected functional groups. Owing to the operationally convenient conditions, virtually complete stereoselectivity, and full recyclability of the source of chirality, this method should find wide applications for the preparation of TM-α-AAs, especially on large scale.

Keywords: N ligands; amino acids; enantioselectivity; kinetic resolution; nickel.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids / metabolism*
  • Kinetics
  • Ligands
  • Molecular Structure
  • Nickel / chemistry*
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Thermodynamics*

Substances

  • Amino Acids
  • Ligands
  • Organometallic Compounds
  • Nickel