Direct catalytic asymmetric reductive amination of simple aromatic ketones

Org Lett. 2013 Sep 6;15(17):4354-7. doi: 10.1021/ol401851c. Epub 2013 Aug 12.

Abstract

A green method for chiral amine synthesis, the direct catalytic asymmetric reductive amination, was developed. Phenylhydrazide is an ideal nitrogen source for reductive amination. Molecular sieves play dual roles in this reaction. They help to remove H2O to form imine, as well as promote an imine reduction. f-Binaphane minimizes the inhibition effect from amines and helps the coordination of sterically demanding imines to the iridium center, thus leading to a smooth reaction.

Publication types

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

MeSH terms

  • Amination
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Catalysis
  • Imines / chemical synthesis*
  • Imines / chemistry
  • Iridium / chemistry
  • Ketones / chemistry*
  • Molecular Structure
  • Phenylhydrazines / chemical synthesis
  • Phenylhydrazines / chemistry
  • Stereoisomerism

Substances

  • Amines
  • Imines
  • Ketones
  • Phenylhydrazines
  • phenylhydrazine
  • Iridium