The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridines. Moreover, the use of alkoxy substituted aziridines opens new routes to non-natural alpha- and beta-amino acids. (C) 2002 Elsevier Science Ltd. All rights reserved.
Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N-Bz Aziridines to Allylic Amides
作者:Song Lin、Devin P. Wood、Weiyang Guan
DOI:10.1055/s-0037-1610779
日期:2021.11
Herein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence
Generation of Nitrene by the Photolysis of <i>N</i>-Substituted Iminodibenzothiophene
作者:Hiroyuki Morita、Atsushi Tatami、Tetsuo Maeda、Byung Ju Kim、Wataru Kawashima、Toshiaki Yoshimura、Hitoshi Abe、Takeshi Akasaka
DOI:10.1021/jo800604t
日期:2008.9.19
To evaluate the ability of dibenzothiophene N-substituted sulfilimines as photochemical nitrene sources, their photolyses in the presence of several trapping reagents, such as sulfides, olefins, and phosphorus compounds, were performed. In the reactions, the corresponding imino-transfer compounds, namely sulfilimines, aziridines, and iminophosphoranes, were formed in good yields, indicating dibenzothiophene N-tosyl and N-acylsulfilimines have a potent nature as nitrogen sources.