740817-87-2Relevant academic research and scientific papers
Aziridination of γ,δ-dibromoethyl-2-pentenoate with primary amines: Extension of the Gabriel-Cromwell reaction
Weller, Rachel L.,Rajski, Scott R.
, p. 5807 - 5810 (2004)
Ethyl (E)-4,5-dibromo-2-pentenoate readily reacts with an assortment of primary amines in the presence of DBU to afford the corresponding conjugated aziridines in good to moderate yields. That the reaction is compatible with a nucleoside-derived amine suggests a broad scope of application.
Photoreactions of β-aziridinylacrylonitriles and acrylates with alkenes: Formation of head-to-head adducts and application to the preparation of pyrrolizidine alkaloid
Ishii, Keitaro,Sone, Takuya,Shimada, Yukio,Shigeyama, Takahide,Noji, Masahiro,Sugiyama, Shigeo
, p. 10887 - 10898 (2007/10/03)
The photochemical C,C-bond cleavage of N-benzyl β- aziridinylacrylonitrile 1 and acrylate 2 and the subsequent [3+2] cycloaddition with electron-deficient alkenes afforded head-to-head adducts selectively and efficiently. Irradiation of N-phenyl aziridine 3 with acrylonitrile gave adducts, but photoreaction of N-benzoyl aziridine 4 and thermal reactions of 3 and 4 with alkenes yielded C(γ),N-cleaved products instead of cycloadducts. N-trityl aziridine 5 also reacted with electron-deficient alkenes, affording 2,3-cis-pyrrolidine derivatives exclusively. A formal synthesis of a pyrrolizidine alkaloid, isoretronecanol (27), starting from 5 was achieved in a convenient manner.
