Intramolecular N-Me and N-H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles

Org Biomol Chem. 2021 Jan 28;19(3):557-560. doi: 10.1039/d0ob02122a.

Abstract

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a variety of 2,3-disubstituted aminoether O-heterocyclic scaffolds, including tetrahydrofurans, tetrahydropyrans and chromanes.

Publication types

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

MeSH terms

  • Chemistry Techniques, Synthetic
  • Ethers / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Hydrogen / chemistry
  • Nitrogen / chemistry*
  • Stereoisomerism

Substances

  • Ethers
  • Heterocyclic Compounds
  • Hydrogen
  • Nitrogen