76325-79-6Relevant academic research and scientific papers
New Mesoporous silica-supported organocatalysts based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, reusable, and heterogeneous catalysts for the asymmetric aldol reaction
Juaristi, Eusebio,Romero-Sedglach, Kevin A.,Sánchez-Antonio, Omar,Vázquez-Orta, Erika C.
, (2020/10/18)
Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol rea
Development of C2-Symmetric Chiral Bifunctional Triamines: Synthesis and Application in Asymmetric Organocatalysis
Ca?ellas, Santiago,Alonso, Pedro,Pericàs, Miquel à.
supporting information, p. 4806 - 4810 (2018/08/24)
The synthesis and application of a newly designed C2-symmetric chiral bifunctional triamine family (C2-CBT) is reported. These enantiopure chiral triamine scaffolds can be accessed in multigram amounts from simple amino acids while avoiding chromatographic purification. As a proof of principle, C2-CBT has been studied in the aldol reaction of cyclic ketones with isatins, with the target tertiary alcohols being formed in a highly efficient manner. Catalyst recovery by simple extraction techniques and subsequent reuse has been performed.
(R)- and (S)-Proline-Derived Chiral Phosphoramides as Organo catalysts for the Enantiodivergent Aldol Reaction of Isatins with Cyclohexanone in the Presence of Water
Cruz-Hernández, Carlos,Hernández-González, Perla E.,Juaristi, Eusebio
supporting information, p. 1827 - 1840 (2018/02/14)
Novel organocatalysts derived from (R)- and (S)-proline and incorporating a chiral phosphoramide fragment were rationally designed and subsequently synthesized. These chiral compounds catalyze the enantioselective aldol addition reaction of cyclohexanone
Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones
Kimura, Jo,Subba Reddy, Ummareddy Venkata,Kohari, Yoshihito,Seki, Chigusa,Mawatari, Yasuteru,Uwai, Koji,Okuyama, Yuko,Kwon, Eunsang,Tokiwa, Michio,Takeshita, Mitsuhiro,Iwasa, Tatsuo,Nakano, Hiroto
, p. 3748 - 3756 (2016/08/16)
Enantioselective aldol reactions of various isatins with ketones using newly designed amino amide organocatalysts were found to provide chiral 3-substituted 3-hydroxy-2-oxindoles in good to excellent yields and with excellent stereoselectivities (up to 99 %, up to 98 % ee, syn/anti = 99:1); one catalyst, 3i, proved particularly successful. One of the resulting oxindoles, 3-hydroxy-3-(2-oxocyclohexyl)-2-indolinone may serve as a synthetic intermediate for pharmaceutically important compounds and, in its own right, shows interesting anticonvulsant activities.
2-Azanorbornane-based amine organocatalyst for enantioselective aldol reaction of isatins with ketones
Ogasawara, Ayumi,Subba Reddy,Seki, Chigusa,Okuyama, Yuko,Uwai, Koji,Tokiwa, Michio,Takeshita, Mitsuhiro,Nakano, Hiroto
, p. 1062 - 1068 (2016/10/11)
Optically active 2-azanorbornane-based organocatalysts were designed and synthesized, and the catalytic activity of these catalysts in enantioselective aldol reactions of isatins with ketones was investigated. Among these catalysts, 2-azanorbornylmethanol
Enzymatic enantioselective aldol reactions of isatin derivatives with cyclic ketones under solvent-free conditions
Liu, Zhi-Qiang,Xiang, Zi-Wei,Shen, Zhou,Wu, Qi,Lin, Xian-Fu
, p. 156 - 160 (2014/05/06)
Nuclease p1 from Penicillium citrinum was observed to directly catalyze the asymmetric aldol reactions between isatin derivatives and cyclic ketones with high isolated yields (up to 95%) and moderate to good stereoselectivity (dr up to >99/1, ee up to 82%
In situ formed bifunctional primary amine-imine catalyst: Application to the construction of chiral tertiary alcohols through asymmetric aldol-type reaction
Mao, Zhijie,Zhu, Xi,Lin, Aijun,Li, Weipeng,Shi, Yan,Mao, Haibin,Zhu, Chengjian,Cheng, Yixiang
supporting information, p. 2029 - 2036 (2013/08/23)
An in situ formation method to obtain chiral bifunctional primary amine-imine catalysts from the C2-symmetric chiral diimines has been developed. The efficiency of this method in the construction of chiral tertiary alcohols which are valuable p
Highly diastereo- and enantioselective direct aldol reaction under solvent-free conditions
Zhang, Furen,Li, Chunmei,Qi, Chenze
, p. 380 - 388 (2013/06/27)
An efficient, solvent-free protocol for the asymmetric aldol reaction between aldehydes and ketones using prolinamides 1-4 as organocatalysts is reported. Catalysts 2-4, in the presence of TFA (the ratio of catalyst and TFA = 1/1.5), proved to be excellen
