New aniline-containing amino alcohols from trans-(R,R)-2-(2-nitrophenyl)-3-phenyloxirane as useful intermediates for the synthesis of chiral ligands, bases, and benzoxazine nucleus

J Org Chem. 2006 Dec 22;71(26):9891-4. doi: 10.1021/jo0617969.

Abstract

New enantiopure aniline-containing amino alcohols are directly derived from trans-(R,R)-2-(2-nitrophenyl)-3-phenyloxirane, by alternative regioselective double reductions. Subsequent selective alkylation procedures and derivatizations provide a rapid and high-yielding access to different chiral ligands, bases, and benzoxazines, without loss of optical purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry
  • Aniline Compounds / chemistry*
  • Benzoxazines / chemical synthesis*
  • Benzoxazines / chemistry
  • Epoxy Compounds / chemistry*
  • Ligands
  • Molecular Conformation
  • Stereoisomerism
  • Stilbenes / chemistry*

Substances

  • 2-(2-nitrophenyl)-3-phenyloxirane
  • Amino Alcohols
  • Aniline Compounds
  • Benzoxazines
  • Epoxy Compounds
  • Ligands
  • Stilbenes
  • aniline