58686-65-0Relevant articles and documents
Metal-Free Oxidative [5+1] Cyclization of 1,5-Enynes for the Synthesis of Pyrazine 1-Oxide
Xia, Xiao-Feng,Zhao, Mingming,He, Wei,Zou, Lianghua,San, Xinxin,Wang, Dawei
supporting information, p. 3621 - 3626 (2020/08/05)
A chemo-selective nitrosylation of 1,5-enynes via a sequence of NO radical incorporation and intramolecular radical cyclization was reported. The formation of two C?N bonds and one C?O bond make this [5+1] cycloaddition reaction an efficient approach to synthesize pyrazine 1-oxides in moderate to good yields. Metal-free, short reaction time and mild conditions render this strategy more practical, eco-friendly and convenient. Synthetic utility of this protocol is highlighted by scaffolds diversification. (Figure presented.).
Gold(I)/Chiral N,N′-Dioxide–Nickel(II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement
Li, Jun,Lin, Lili,Hu, Bowen,Zhou, Pengfei,Huang, Tianyu,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 885 - 888 (2017/01/13)
A highly efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a π-acidic gold(I) complex with a Claisen rearrangement catalyzed by a chiral Lewis acidic N,N′-dioxide–nickel(II) complex. A range of acyclic α-allyl β-keto esters were synthesized in high yields (up to 99 %) with good diastereoselectivities (up to 97:3) and excellent enantioselectivities (up to 99 % ee) under mild reaction conditions. These products can be easily transformed into optically active β-hydroxy esters, β-hydroxy acids, or 1,3-diols.
Design and application of a low-temperature continuous flow chemistry platform
Newby, James A.,Blaylock, D. Wayne,Witt, Paul M.,Pastre, Julio C.,Zacharova, Marija K.,Ley, Steven V.,Browne, Duncan L.
, p. 1211 - 1220 (2014/12/10)
A flow reactor platform technology applicable to a broad range of low temperature chemistry is reported. The newly developed system captures the essence of running low temperature reactions in batch and represents this as a series of five flow coils, each with independently variable volume. The system was initially applied to the functionalization of alkynes, Grignard addition reactions, heterocycle functionalization, and heteroatom acetylation. This new platform has then been used in the preparation of a 20-compound library of polysubstituted, fluorine-containing aromatic substrates from a sequential metalation-quench procedure and can be readily adapted to provide gaseous electrophile inputs such as carbon dioxide using a tube-in-tube reactor.
