928154-76-1Relevant academic research and scientific papers
Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines
Song, Lina,Tian, Xianhai,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 9007 - 9010 (2019)
We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).
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.
