75716-86-8Relevant academic research and scientific papers
2-Oxo-Driven Coupling Reactions of 2-Oxo Aldehydes/2-Oxo Iminium Ions and Hydroperoxides at Room Temperature
Khan, Shahnawaz,Ahmed, Qazi Naveed
, p. 5377 - 5385 (2016/11/22)
An efficient 2-oxo-group-promoted direct coupling reaction between 2-oxo aldehydes and hydroperoxides has been developed. The method has been used successfully for the generation of different 2-oxo esters and acids. This reaction harnesses the hydrogen-bonding-induced self-decomposition tendency of hydroperoxides; the intermediates produced by this process then attack the aldehyde or iminium ion to generate cross-coupled products either by direct coupling or by an amine-catalysed pathway. No external oxidants or metal catalysts are required for our method, and the reaction takes place at room temperature.
Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon-Nitrogen Bond Functionalization
Wang, Shuo-En,Wang, Linfei,He, Qiuqin,Fan, Renhua
supporting information, p. 13655 - 13658 (2015/11/11)
The formation of carbon-carbon bonds through the functionalization of aromatic carbon-nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon-nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para-substituted anilines serve as a potential aryl source in the construction of a range of functionalized aromatic molecules, such as quaternary carbon centers, α-keto esters, and aldehydes.
Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium
Wang, Chao,Zong, Lili,Tan, Choon-Hong
, p. 10677 - 10682 (2015/09/28)
Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize a variety of cationic metal species. In a similar manner, we envision a complementary strategy using chiral cation in partnership with inorganic anionic metal salts. Herein, we report a chiral dicationic bisguanidinium-catalyzed asymmetric oxidation reaction of alkenes with potassium permanganate. Chiral induction is attributed to ion-pairing interaction between chiral cation and enolate anion. The success of the current permanganate oxidation reaction together with mechanistic insights should provide inspiration for expansion to other anionic metal salts and would open up new paradigms for asymmetric transition metal catalysis, phase-transfer catalysis, and ion-pairing catalysis.
Organocatalytic Enantioselective Michael Reaction of Malononitrile with β,β-Disubstituted Nitroalkenes
Chen, Shengwei,Lou, Qinxin,Ding, Yuyang,Zhang, Shasha,Hu, Wenhui,Zhao, Junling
, p. 2437 - 2441 (2015/08/18)
We have developed and optimized an enantioselective Michael reaction of malononitrile with β,β-disubstituted nitroalkenes. This reaction was catalyzed by a cinchona alkaloid derived thiourea catalyst, producing products of high yields (up to 98 %) and ste
Amino Acid Salt Catalyzed Asymmetric Synthesis of 1,2-Diols with A Quaternary Carbon Center
Wu, Quanquan,Liu, Shulei,Wang, Fangyuan,Li, Qingqing,Cheng, Kangli,Li, Juan,Jiang, Jun
, p. 2442 - 2446 (2015/10/19)
Enantioenriched 1,2-diols with a quaternary carbon center have great potential in the preparation of natural and biologically active compounds, but remain challenging synthetic targets which demand for both good diastereo- and enantioselectivity. As part
Chemo- and enantioselective Bronsted acid-catalyzed reduction of α-imino esters with catecholborane
Enders, Dieter,Rembiak, Andreas,Stoeckel, Bianca Anne
supporting information, p. 1937 - 1942 (2013/08/23)
The chemo- and enantioselective reduction of α-imino esters with catecholborane has been developed employing 10 mol% of an enantiopure BINOL-based phosphoric acid as organocatalyst. Various differently substituted aromatic α-amino acid derivatives can be
Catalytic asymmetric transfer hydrogenation of α-ketoesters with hantzsch esters
Yang, Jung Woon,List, Benjamin
, p. 5653 - 5655 (2007/10/03)
C2-symmetric chiral copper(II)-bisoxazolines function as alcohol dehydrogenase mimics and catalyze highly enantioselective transfer hydrogenations of α-ketoesters with Hantzsch esters as a synthetic NADH analogue to give α-hydroxy esters in excellent enantioselectivities.
