928154-51-2Relevant academic research and scientific papers
Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams
Yeh, Ming-Chang P.,Shiue, Yuan-Shin,Lin, Hsin-Hui,Yu, Tzu-Yu,Hu, Ting-Chia,Hong, Jia-Jyun
supporting information, p. 2407 - 2410 (2016/06/09)
A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.
Synthesis of 3-aza-bicyclo[3.1.0]hexan-2-one derivatives via gold-catalyzed oxidative cyclopropanation of N -allylynamides
Wang, Kai-Bing,Ran, Rui-Qiao,Xiu, Shi-Dong,Li, Chuan-Ying
, p. 2374 - 2377 (2013/06/27)
N-Allylynamides with various functional groups and different substitution patterns can be converted into 3-aza-bicyclo[3.1.0]hexan-2-one derivatives in moderate to high yield using IMesAuCl/AgBF4 as the catalyst and pyridine N-oxide as the oxidant. A noncarbene mediated approach is proposed as the mechanism.
Silylcupration and copper-catalyzed carbomagnesiation of ynamides: Application to aza-Claisen rearrangement
Yasui, Hiroto,Yorimitsu, Hideki,Oshima, Koichiro
body text, p. 373 - 379 (2009/04/07)
Treatment of ynamides with silylcopper reagents resulted in silylcupration to afford (E)-ss-silylenamides, after protonolysis, in good yields with high regio- and stereoselectivity. Reaction of ynamides having an allyl group on the nitrogen with Grignard reagents in the presence of a copper catalyst resulted in carbomagnesiation across the alkynyl unit and subsequent heating provided 4-pentenenitriles via aza-Claisen rearrangement.
