Synthesis of optically active deuterated primary amines via reduction of N-tert-butanesulfinyl aldimines

J Org Chem. 2014 Sep 5;79(17):8417-21. doi: 10.1021/jo500767k. Epub 2014 Aug 11.

Abstract

Optically active deuterated primary amines have been obtained with 78-98% ee's from chiral N-tert-butanesulfinyl aldimines via reduction with N-Selectride and subsequent alcoholysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Catalysis
  • Digitonin / chemistry*
  • Imines / chemistry*
  • Lysine / chemistry*
  • Molecular Structure
  • Semicarbazides / chemistry*
  • Stereoisomerism
  • Sulfhydryl Reagents / chemistry*
  • Valine / chemistry*

Substances

  • Amines
  • Imines
  • Semicarbazides
  • Sulfhydryl Reagents
  • aldimine eliminator
  • Valine
  • Lysine
  • Digitonin