128541-14-0Relevant academic research and scientific papers
Intramolecular Cyclopropanation: Stereospecific Synthesis of (E)- and (Z)-1-Aminocyclopropane-1-carboxylic Acids
Koskinen, Ari M. P.,Munoz, Luis
, p. 879 - 886 (1993)
tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields.The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclohexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 15 via Curtius- or Hoffmann-type rearrangements, respectively.The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40percent overall from malonic acid).The free amino acids 12 and 13 can be liberated in two steps.
