75716-84-6Relevant 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.
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
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.
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
Diastereodivergent addition of allenylzincs to aryl glyoxylates
Hameury, Thomas,Guillemont, Jerome,Hijfte, Luc Van,Bellosta, Veronique,Cossy, Janine
supporting information; experimental part, p. 2397 - 2400 (2009/10/10)
A diastereodivergent addition of allenylzincs to aryl glyoxylates was observed depending on the method used for the preparation of the allenylzinc reagent. The allenylzincs were prepared from propargylic benzoates in the presence of a palladium catalyst o
Organocatalytic asymmetric transferhydrogenation of β-nitroacrylates: Accessing β2-amino acids
Martin, Nolwenn J. A.,Cheng, Xu,List, Benjamin
supporting information; experimental part, p. 13862 - 13863 (2009/02/06)
We describe a highly efficient and enantioselective Hantzsch ester mediated conjugate reduction of β-nitroacrylates that is catalyzed by a Jacobsen thiourea catalyst as a key step in a new route to optically active β2-amino acids. Copyright
