75716-85-7Relevant academic research and scientific papers
Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling
Yamada, Tsuyoshi,Kuwata, Marina,Takakura, Ryoya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 637 - 641 (2017/12/13)
A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).
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.
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
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
Asymmetric friedel-crafts alkylation of α-substituted β-nitroacrylates: Access to β2,2-amino acids bearing indolic all-carbon quaternary stereocenters
Weng, Jian-Quan,Deng, Qiao-Man,Wu, Liang,Xu, Kai,Wu, Hao,Liu, Ren-Rong,Gao, Jian-Rong,Jia, Yi-Xia
, p. 776 - 779 (2014/03/21)
A highly enantioselective Friedel-Crafts alkylation reaction of indoles with acyclic α-substituted β-nitroacrylates is developed under the catalysis of Ni(ClO4)2-bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to β2,2-amino ester and tetrahydro-β-carboline through nitro reduction and sequential Pictet-Spengler cyclization was exemplified.
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.
