Aminodiols via stereocontrolled oxidation of methyleneaziridines

Org Lett. 2014 Mar 21;16(6):1696-9. doi: 10.1021/ol5003576. Epub 2014 Mar 11.

Abstract

A highly diastereoselective Ru-catalyzed oxidation/reduction sequence of bicyclic methyleneaziridines provides a facile route to complex 1-amino-2,3-diol motifs. The relative anti stereochemistry between the amine and the vicinal alcohol are proposed to result from 1,3-bischelation in the transition state by the C1 and C3 heteroatoms.

Publication types

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

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aziridines / chemistry*
  • Carbamates / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Structure
  • Oxidation-Reduction
  • Ruthenium / chemistry
  • Stereoisomerism

Substances

  • Alcohols
  • Aziridines
  • Carbamates
  • Ruthenium