871828-95-4Relevant academic research and scientific papers
Modular Design of Chiral Conjugate-Base-Stabilized Carboxylic Acids: Catalytic Enantioselective [4 + 2] Cycloadditions of Acetals
Abboud, Khalil A.,Kirm, Helmi-Ulrika,Leito, Ivo,Odagi, Minami,Saame, Jaan,Seidel, Daniel,Supantanapong, Nantamon,Xu, Weici,Zhu, Zhengbo
supporting information, p. 15252 - 15258 (2020/10/18)
Readily available 1,2-amino alcohols provide the framework for a new generation of chiral carboxylic acid catalysts that rival the acidity of the widely used chiral phosphoric acid catalyst (S)-TRIP. Covalently linked thiourea sites stabilize the carboxyl
Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
Tan, Wei,Wei, Jianpeng,Jiang, Xuefeng
supporting information, p. 2166 - 2169 (2017/04/27)
An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
Hydrogen Bonding Networks in Chiral Thiourea Organocatalysts: Evidence on the Importance of the Aminoindanol Moiety
Gimeno, M. Concepción,Herrera, Raquel P.
, p. 5091 - 5099 (2016/10/12)
The crystal structures of four chiral thioureas, which are normally used as organocatalysts, are reported by the first time. Each compound is assembled in the crystal in a different way according to their chiral moiety in the thiourea skeleton, being depe
Exploiting molecular self-assembly: From urea-based organocatalysts to multifunctional supramolecular gels
Schoen, Eva-Maria,Marques-Lopez, Eugenia,Herrera, Raquel P.,Aleman, Carlos,Diaz, David Diaz
, p. 10720 - 10731 (2014/11/08)
We describe the self-assembly properties of chiral N,N′-disubstituted urea-based organocatalyst 1 that leads to the formation of hierarchical supramolecular gels in organic solvents at low concentrations. The major driving forces for the gelation are hydr
Evaluating Thiourea Architecture for Intramolecular [2+2] Photocycloaddition of 4-Alkenylcoumarins
Vallavoju, Nandini,Selvakumar, Sermadurai,Jockusch, Steffen,Prabhakaran, Manoj Thathamkulam,Sibi, Mukund P.,Sivaguru, Jayaraman
supporting information, p. 2763 - 2768 (2016/02/18)
The efficiency of [2+2] photocycloadditions of 4-alkenylcoumarins was evaluated with various thiourea skeletons to develop thiourea-based catalysts for promoting photochemical reactions. Our results indicate that the excited state chemistry is dependent o
Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes
Alcaine, Ana,Marques-Lopez, Eugenia,Merino, Pedro,Tejero, Tomas,Herrera, Raquel P.
scheme or table, p. 2777 - 2783 (2011/05/04)
Bifunctional thiourea catalyzes the enantioselective Michael addition reaction of diphenyl phosphite to nitroalkenes. This methodology provides a facile access to enantiomerically enriched β-nitrophosphonates, precursors for the preparation of synthetically and biologically useful β-aminophosphonic acids. DFT level of computational calculations invoke the attack of the diphenyl phosphite to the nitroolefin by the Re face, this give light to this scarcely explored process update in the literature. The computational calculations support the absolute configuration obtained in the final adducts.
Enhanced efficiency of thiourea catalysts by external Bronsted acids in the Friedel-Crafts alkylation of indoles
Marques-Lopez, Eugenia,Alcaine, Ana,Tejero, Tomas,Herrera, Raquel P.
supporting information; experimental part, p. 3700 - 3705 (2011/09/14)
A novel study on the influence of external Bronsted acids on thiourea catalysts in the asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes is reported. The final 3-substituted indole derivatives were synthesized with better results because o
Asymmetric diels-alder reactions of vinylindoles using organocatalysis
Gioia, Claudio,Bernardi, Luca,Ricci, Alfredo
experimental part, p. 161 - 170 (2010/04/28)
The different behavior of 3- and 2-vinylindoles in Diels-Alder cycloaddition reactions in the presence of bifunctional hydrogen bond donor organocatalysts is described.
Organocatalysis in conjugate amine additions. Synthesis of β-amino acid derivatives
Sibi, Mukund P.,Itoh, Kennosuke
, p. 8064 - 8065 (2008/02/09)
Conjugate addition of O-protected hydroxylamines to pyrazole-derived enoates proceeds with high efficiency and enantioselectivity when chiral thioureas are used as activators. A wide variety of substrates undergo conjugate amine addition providing access to enantioenriched β-amino acid derivatives. Structural requirements for the optimal thiourea catalyst have been established, and the results suggest that it operates as a bifunctional catalyst. Copyright
Asymmetric Morita-Baylis-Hillman reaction catalyzed by simple amino alcohol derived thioureas
Lattanzi, Alessandra
, p. 2106 - 2110 (2008/02/09)
Thioureas straightforwardly derived from commercially available enantiopure amino alcohols have been found to promote the asymmetric Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one and different aldehydes in the presence of triethylamine under solven
