810665-85-1Relevant articles and documents
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.
