Intramolecular radical trapping in “set” ring opening of N-enoyl aziridines. A new mechanistic probe and a new synthesis of pyrrolidones.
作者:G. Bentz、N. Besbes、A. Laurent、H. Stamm
DOI:10.1016/s0040-4039(00)95454-6
日期:1987.1
N-Acryloyl aziridines 1a-c form pyrrolidones 4a-c via electron attachment, homolytic ring cleavage of the intermediate ketyl, and intramoleculartrapping of the radical by the CC bond of the acryloyl moiety of 1a-c.
A New Convenient Method for the Preparation of Enamides from<i>N</i>-Allylamides
作者:Manfred Hesse、Sergey Sergeyev
DOI:10.1055/s-2002-32962
日期:——
Isomerization of various N-allylamides in the presence of Fe(CO)5 smoothly afforded the corresponding enamides in yields up to 95%. The reported procedure is compatible with various functional groups including protected amino and hydroxy groups. The possible mechanism of transformation is discussed.
Synthesis of polysubstituted enamides via metal-catalyzed hydrogen atom transfer by merger of cobalt/photoredox catalysis was achieved. The judicious choice of Co(3-tert-butyl-5-CF3-salophen) and Co(3,5-di-tert-butylsalophen) enabled access to polysubstituted enamides. The method tolerated haloarenes, heteroarenes, free hydroxy groups, non-protected indoles, and drug-like molecules. Furthermore, this