20765-23-5Relevant academic research and scientific papers
Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline
Shi, Hui,Du, Chuan,Zhang, Xinhang,Xie, Fukai,Wang, Xiaoyu,Cui, Shanshan,Peng, Xiaoshi,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
, p. 1312 - 1319 (2018/02/09)
A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations. The application of the methodology was demonstrated by the efficient one-pot synthesis of (±)-latifine and (±)-cherylline, both are 4-aryltetrahydroisoquinoline alkaloids isolated from Amaryllidacecae plants.
Selective Metal-Free Deoxygenation of Unsymmetrical 1,2-Dicarbonyl Compounds by Chlorotrimethylsilane and Sodium Iodide
Yuan, Ling-Zhi,Renko, Dolor,Khelifi, Ilhem,Provot, Olivier,Brion, Jean-Daniel,Hamze, Abdallah,Alami, Mouad
supporting information, p. 3238 - 3241 (2016/07/14)
For the first time, the combination of chlorotrimethylsilane with NaI is used as a selective reducting system toward 1,2-diketones. This combination is successfully evaluated with several unsymmetrically benzil derivatives, which are reduced in good yield
Flavonoids. 43. Deprotonation-initiated Aryl Migration with Sulfur Dioxide Extrusion: A Route to 2,3-Dihydro-2,3-diaryl-3-hydroxy-4H-1-benzopyran-4-ones
Patonay, Tamas,Hegedues, Laszlo,Patonay-Peli, Erzsebet
, p. 145 - 151 (2007/10/02)
Treatment of trans-2,3-dihydro-2-aryl-3-nosyloxy-4H-1-benzopyran-4-ones with various bases afforded 2,3-dihydro-r-2-aryl-t-3-hydroxy-c-3-(4-nitrophenyl)-4H-1-benzopyran-4-ones in a deprotonation-initiated aryl migration followed by sulfur dioxide extrusion.In the presence of hydroxide and methoxide ions a secondary ring cleavage has also been observed.However, the reaction of trans-2,3-dihydro-2-aryl-3-nosyloxy-4H-1-benzopyran-4-ones with cyanide ions gave 2,3-dihydro-r-2-aryl-t-4-cyano-c-3,c-4-epoxy-4H-1-benzopyrans in a carbonyl attack of cyanide followed by an internal substitution reaction.
