Enantioselective synthesis of new chiral 2-aziridinyl phosphonates and studies of their biological activities

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

“…ATR data were reported in cm −1 . N ‐alkyl substituted aziridine‐2‐phosphonates were prepared according to a published procedure …”

“…Although the literature have many examples to ring opening reactions of aziridine‐2‐carboxylates, the same reaction studied with the aziridine‐2‐phosphonates are limited . Our group is also involved in this field and reported the synthesis of racemic and chiral aziridine‐2‐phosphonates by modified Gabriel–Cromwell reaction and the results of their antibacterial activities . Our efforts in related chemistry continued with the ring opening reaction of aziridine‐2‐phosphonates by HCl which resulted in the formation of β ‐chloro‐ α ‐amino phosphonates .…”

Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

“…Aziridine 2-phosphonates 1a-1i were prepared by the modified GabrielÀ Cromwell reaction starting from vinyl phosphonate or α-tosylvinyl phosphonate as reported by our group. [21,22] For the conversion of phosphonates to phosphonic acid derivatives, different hydrolysis conditions were examined. First, aziridine 2-diethylphosphonates were heated with KOH at 100°C then passed through a Dowex column.…”

“…TLC plate was stained with phosphomolybdic acid solution in ethanol. All the aziridine‐2‐phosphonates 1a – 1i were prepared as reported in the literature …”

“…1 H-, 13 C-, and 31 were prepared as reported in the literature. [21,22] General Procedure for the Preparation of Aziridinyl Phosphonic Acids 2a-2i…”