332902-04-2Relevant articles and documents
The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α-Difluoro-β-amino Amides
Zhang, Rui,Zhang, Zhikun,Zhou, Qi,Yu, Lefei,Wang, Jianbo
, p. 5744 - 5748 (2019/03/28)
Fluorine-containing β-amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the
Isocyanate stabilizer and preparation method thereof
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Paragraph 0052; 0053; 0054, (2018/06/21)
The invention relates to an isocyanate stabilizer and a preparation method thereof, aiming at inhibiting yellowing and turbidity phenomena caused by the fact that isocyanate is in contact with water and oxygen in a downstream utilization process. The isoc
Nickel(0)-Catalyzed Hydroalkenylation of Imines with Styrene and Its Derivatives
Xiao, Li-Jun,Zhao, Chao-Yue,Cheng, Lei,Feng, Bo-Ya,Feng, Wei-Min,Xie, Jian-Hua,Xu, Xiu-Fang,Zhou, Qi-Lin
supporting information, p. 3396 - 3400 (2018/03/01)
A nickel(0)-catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a new atom- and step-economical approach to allylic amines by using alkenes instead of alkenyl-metallic reagents. Experiments and DFT calculations showed that TsNH2 promotes the proton transfer from the coordinated olefin to the imine, accompanied by a new C?C bond formation.
Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines
Shikora, Jonathan M.,Chemler, Sherry R.
, p. 2133 - 2137 (2018/04/30)
A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.
Dual gold catalysis: A novel synthesis of bicyclic and tricyclic pyrroles from n -propargyl ynamides
Tokimizu, Yusuke,Wieteck, Marcel,Rudolph, Matthias,Oishi, Shinya,Fujii, Nobutaka,Hashmi, A. Stephen K.,Ohno, Hiroaki
supporting information, p. 604 - 607 (2015/03/05)
Various N-propargyl ynamides were converted to bicylic and tricyclic pyrroles by the use of a cationic dual-activation gold catalyst. This reaction starts with the nucleophilic addition of a gold acetylide onto an ynamide triple bond at the ?2-position of the nitrogen atom. Thus, gold vinylidene is formed, and then a second cyclization takes place. The formation of the gold vinylidene is indicated by the evidence that not only aryl ynamides but also alkyl ynamides undergo C-H activation in these reactions.
Chiral diphosphane- and NHC-containing ruthenium catalysts for the catalytic asymmetric arylation of aldimines with organoboron reagents
Marques, Carolina S.,Burke, Anthony J.
supporting information; experimental part, p. 4232 - 4239 (2012/09/22)
For the first time, we report the application of [RuCl2(η 6-p-cymene)]2 in the arylation of N-activated aldimines with boronic acids and its derivatives to afford chiral amines, which are important intermediates in the syntheses of key bioactive compounds. The behavior of the chiral ligands, the imine substrates, and the organoboron reagents were studied. Very good enantioselectivities were obtained. A new method is presented for the synthesis of chiral substituted amines by employing Ru catalysts along with known chiral phosphane ligands and a new NHC-type chiral ligand. Organoboron reagents were applied as the aryl transfer agents. High enantioselectivities were achieved with this new method, and some mechanistic insights are provided.
Highly enantioselective arylation of N -tosylalkylaldimines catalyzed by rhodium-diene complexes
Cui, Zhe,Yu, Hong-Jie,Yang, Rui-Feng,Gao, Wen-Yun,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information; experimental part, p. 12394 - 12397 (2011/10/02)
A highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines has been developed. The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions is the key to achieving high yield and enantioselectivity. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure. Furthermore, excellent results are also obtained for the imine substrates with the more readily cleavable N-nosyl protecting group.
Efficient and convenient preparation of N-tosylimines catalyzed by indium trichloride
Deng, Gui Sheng,Zou, Jing Yuan,Sun, Teng Fei
scheme or table, p. 511 - 514 (2012/01/05)
A new method for preparation of N-tosylimines by InCl3-mediated condensation of aldehydes with p-toluenesulfonamide in refluxing benzene is reported. The procedure is lauded by its simplicity, mild reaction conditions, excellent yields and adap
Iron-catalyzed sulfonylimine synthesis under neutral conditions
Wu, Xiao-Feng,Vovard-Le Bray, Chloé,Bechki, Lazhar,Darcel, Christophe
experimental part, p. 7380 - 7384 (2009/12/06)
A convenient FeCl3-catalyzed synthesis of N-sulfonylimines via the condensation of aldehydes with N-sulfonylamides in mild and neutral conditions (in ethanol at room temperature) is reported. This procedure constitutes the first iron-catalyzed
Base and copper(i) catalyzed Mannich, alkyne hydroamination cascades for the direct synthesis of 2-methylenepyrrolidines
Wang, Hai-Fei,Yang, Ting,Xu, Peng-Fei,Dixon, Darren J.
supporting information; experimental part, p. 3916 - 3918 (2010/01/06)
An efficient, simple-to-perform, one-pot reaction cascade to 2-methylenepyrrolidines from p-toluenesulfonyl protected imines and propargylated malonates under a combination of base and copper(i) catalysis is reported.