928154-48-7Relevant academic research and scientific papers
Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes
Shcherbakov, Nikolay V.,Dar'In, Dmitry V.,Kukushkin, Vadim Yu.,Dubovtsev, Alexey Yu.
, p. 12964 - 12972 (2021/09/18)
The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.
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.
