Synthesis of enantiopure 3-substituted morpholines

J Org Chem. 2010 Nov 5;75(21):7454-7. doi: 10.1021/jo101339g.

Abstract

Enantiopure 3-substituted morpholines were assembled through ring-opening of a N-2-benzothiazolesulfonyl (Bts) activated aziridine with organocuprates followed by a ring annulation reaction with a vinylsulfonium salt under microwave conditions. Deprotection of the N-Bts group proceeds under very mild conditions with 2-mercaptoacetic acid and LiOH at rt.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzothiazoles / chemistry
  • Morpholines / chemical synthesis*
  • Morpholines / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Benzothiazoles
  • Morpholines
  • morpholine
  • benzothiazole