Effenberger, FranzKühlwein, JürgenBaumgartner, Christian2009-08-282016-03-312009-08-282016-03-31199431628324Xhttp://nbn-resolving.de/urn:nbn:de:bsz:93-opus-44623http://elib.uni-stuttgart.de/handle/11682/1194http://dx.doi.org/10.18419/opus-11772-Isocyanato-2-alkenoates 3 were obtained in good yields by the perrhenate-catalyzed decomposition of 2-azidoalkanoates 1 in the presence of diphosgene (2a) or phosgene (2b). Methyl 2-azidopropionate (1h) reacts to give a mixture of methyl 2-isocyanato-2-propenoate (3h) and methyl 2-chloro-2-isocyanatopropionate (4). The addition product 4 could easily be converted into 3h by elimination of HCl with triethylamine at 0°C. With benzyl alcohol (5a) and tert-butyl alcohol (5b) the isocyanates 3 react smoothly to give the corresponding Z- or Boc-protected 2,3-didehydroamino acid esters 6 and 7, respectively. The acrylic acid derivative 3h reacts as dienophile with various dienes to yield the Diels-Alder adducts 8-10.deinfo:eu-repo/semantics/openAccessAlkene , Aminosäuren540article