Application of intramolecular 1,3-dipolar cyclic addition of azide and olefin; construction of (pyrrolidine-2-ylidene)glycinate and glycinamides

Chem Pharm Bull (Tokyo). 2005 May;53(5):529-36. doi: 10.1248/cpb.53.529.

Abstract

Oxopropyl E-(pyrrolidine-2-ylidene)glycinamide (5c) and allyl E-(pyrrolidine-2-ylidene)glycinate (5d) were effectively synthesized from 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl(TBDMS)-D-arabinal (7) using intramolecular 1,3-dipolar cyclic reaction of azide and olefin as a key reaction. These results proved this cyclic reaction should be applicable for the synthesis of various (pyrrolidine-2-ylidene)glycinate and glycinamide. In addition, the development of a synthetic route for the precursor of an unsaturated cyclic dehydro amino acid involved in azinomycins (carzinophilin) using relating glycinate, methyl E-(pyrrolidine-2-ylidene)glycinate (5a) was described.

MeSH terms

  • Alkenes / chemistry*
  • Azides / chemistry*
  • Glycine / analogs & derivatives*
  • Glycine / chemistry
  • Pyrrolidines / chemistry*

Substances

  • Alkenes
  • Azides
  • Pyrrolidines
  • glycine amide
  • Glycine