87876-90-2Relevant academic research and scientific papers
Direct α-C-H bond functionalization of unprotected cyclic amines
Chen, Weijie,Ma, Longle,Paul, Anirudra,Seidel, Daniel
, p. 165 - 169 (2018/02/06)
Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.
A NEW SYNTHESIS OF IMIDOYL IODIDES VIA BECKMANN REARRANGEMENT OF OXIME SULFONATES
Ishida, Yasuko,Sasatani, Satoru,Maruoka, Keiji,Yamamoto, Hisashi
, p. 3255 - 3258 (2007/10/02)
A new synthetic method of imidoyl iodides has been devised which involves the Beckmann rearrangement of oxime derivatives with trimethylsilyl iodide or diethylaluminum iodide.This allows a one-pot procedure for α-arylation of amines in synthetically usefu
