The Reaction of α,β-Dibromo Acid Esters with Benzylamine

Regiospecific and Enantiospecific Ring Opening of Methyl (+)-(1'R, 2R)- and (-)-(1'R, 2S)-1-(2-phenylethanol) Aziridine-2-carboxylates

“…In addition, this allowed the precise measurement of coupling constants. Important differences in chemical shifts were found in the 1 H NMR spectra for (3HCl) and (4HCl) hydrochlorides after addition of DMSO-d 6 . These results confirm that each diasteromer was obtained in pure form and has a particular 1 H NMR spectrum that can be clearly identified (Scheme 2.…”

“…Two sets of 1 H NMR spectra were performed for compound (3HCl); a dramatic improvement in resolution was achieved after addition of a small amount of DMSO-d 6 . In addition, this allowed the precise measurement of coupling constants.…”

“…To the present, the mentioned reaction shows more often poor regioselectivity and it is less common to find reports where the ring-opening of aziridines occurs with high regio-and stereospecificity. [5][6][7][8].…”

Synthese und Eigenschaften von Aziridincarbonsäureestern

“…Beschrieben waren dagegen N-benzylierte Ester vom Typus 3, die von STOLBERG [3], in Anlehnung an die Arbeiten von CROMWELL [4], hergestellt von Cycloserin zu benutzen. Die Substituenten am N-Atom (Benzyl bzw.…”

“…20% Ausbeute erhielt. Irn Laboratoriurn ist aber die vorher beschriebene Verwendung der vie1 leichter reagierenden Bromestet vorzuziehen.Verwendet man in Analogie zu den Arbeiten von STOLBERG[3] mit Amrnoniak gesattigte Losungsrnittel wie Ather, Benzal, Chloroform, Tetrahydrofuran usw., so bleibt die Reaktion bei den a-Chlor-bzw. or-Brom-acrylestern stehen.…”