83976-44-7Relevant academic research and scientific papers
Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts
Mahato, Chandan K.,Mukherjee, Sayan,Kundu, Mrinalkanti,Vallapure, Virbhadra P.,Pramanik, Animesh
, p. 5213 - 5226 (2021/05/05)
Organic transformations exclusively in water as an environmentally friendly and safe medium have drawn significant interest in the recent years. Moreover, transition metal-free synthesis of enantiopure molecules in water will have a great deal of attentio
A development of a reusable copper supported imidazolium functionalized ionic liquid catalyzed asymmetric Michael addition reaction
Bharathi Priya, Velumani,Karthikeyan, Parasuraman,Ramya, Subramani,Uthayanila, Selvarasu
, (2021/11/23)
An eco-friendly copper supported Imidazolium functionalized ionic liquid [[Gmim]Cl–Cu (II)] used as green catalyst in solvent free asymmetric Michael addition at 25OC. This technique covers simplified product isolation, high conversion and cata
Chiral anthranilic pyrrolidine as custom-made amine catalyst for enantioselective Michael reaction of nitroalkenes with carbonyl compounds
Moriyama, Katsuhiko,Oka, Yukari,Tsuzuki, Seiji
supporting information, p. 11457 - 11460 (2021/11/12)
A chiral anthranilic pyrrolidine catalyst as a custom-made amine-catalyst was developed for the enantio- and diastereo selective Michael reaction of nitroalkenes with carbonyl compounds. In particular, a peptide-like catalyst in which an α-amino acid is a
Catalytic asymmetric synthesis of chiral covalent organic frameworks from prochiral monomers for heterogeneous asymmetric catalysis
Dong, Yu-Bin,Wang, Jian-Cheng,Kan, Xuan,Shang, Jin-Yan,Qiao, Hua
supporting information, p. 16915 - 16920 (2020/11/09)
Direct synthesis, postsynthetic modification, and chiral induction have been recognized as three powerful methods to synthesize chiral covalent organic frameworks (CCOFs). However, catalytic asymmetric methodology, as the most important and effective synt
Multifunctional phosphoramide-(S)-prolinamide derivatives as efficient organocatalysts in asymmetric aldol and Michael reactions
Cruz-Hernández, Carlos,Landeros, José M.,Juaristi, Eusebio
supporting information, p. 5455 - 5465 (2019/04/05)
The synthesis and evaluation of three novel chiral organocatalysts derived from (S)-proline and containing a bis-amidophosphoryl amine fragment are reported. The structure and conformation of the new compounds were determined by NMR spectroscopy and X-ray crystallographic analysis. The present study represents an effort directed to enhance the performance of (S)-proline-derived organocatalysts in asymmetric aldol and Michael reactions by means of increased steric interactions arising from the incorporation of naphthyl moieties in the catalysts. In the event, the stereoselectivity achieved with naphthyl substituents turned out to be rather similar to that obtained with phenyl analogs. Nevertheless, the new organocatalysts exhibited rather good enantio- and diastereoselectivities in aldol reactions with various isatins and aryl carbaldehydes, affording products with up to 94?:?6 diastereomeric ratios and enantiomeric ratios as high as 95?:?5. Furthermore, products obtained from Michael addition reactions exhibited up to 96?:?4 diastereomeric ratios and enantiomeric ratios as high as 98?:?2.
Chiral Pyrrolidine Bridged Polyhedral Oligomeric Silsesquioxanes as Heterogeneous Catalysts for Asymmetric Michael Additions
Luanphaisarnnont, Torsak,Hanprasit, Sasikarn,Somjit, Vetiga,Ervithayasuporn, Vuthichai
, p. 779 - 786 (2018/01/04)
Abstract: A chiral pyrrolidine bridged polyhedral oligomeric silsesquioxane (SQ) was synthesized, characterized, and used as an effective heterogeneous catalyst. The synthesis involves two simple steps: nucleophilic substitution between benzylchloride fun
Synthesis of a New N-Diaminophosphoryl-N'-[(2S)-2-pyrrolidinylmethyl]thiourea as a Chiral Organocatalyst for the Stereoselective Michael Addition of Cyclohexanone to Nitrostyrenes and Chalcones – Application in Cascade Processes for the Synthesis of Polyc
Cruz-Hernández, Carlos,Martínez-Martínez, Eduardo,Hernández-González, Perla E.,Juaristi, Eusebio
supporting information, p. 6890 - 6900 (2018/11/23)
A highly diastereoselective and enantioselective Michael addition of enolizable ketones such as cyclohexanone and acetophenone to a variety of substituted trans-?-nitrostyrenes and chalcones was catalyzed by a novel chiral and unsymmetrical thiourea as or
Pyrrolidine-carbamate based new and efficient chiral organocatalyst for asymmetric Michael addition of ketones to nitroolefins
Kaur, Amarjit,Singh, Kamal Nain,Sharma, Esha,Shilpy,Rani, Poonam,Sharma, Sandeep Kumar
, p. 6137 - 6143 (2018/09/29)
The novel ((S)-pyrrolidin-2-yl)methyl phenylcarbamate was synthesized and used as an efficient organocatalyst for the asymmetric Michael addition of cyclic/acyclic ketones to nitroolefins. Interestingly, the resulting Michael adducts were obtained in good to high yields (up to 96%) with excellent stereoselectivity (ee up to >99%, dr up to >99:1) without using any additive.
Michael addition of carbonyl compounds to nitroolefins under the catalysis of new pyrrolidine-based bifunctional organocatalysts
Castán,Badorrey,Gálvez,López-Ram-De-Víu,Díaz-De-Villegas
, p. 924 - 935 (2018/02/19)
Novel bifunctional pyrrolidine-based organocatalysts for the asymmetric Michael addition of carbonyl compounds to nitroolefins have been synthesised from homoallylamines, which are easily obtained from (R)-glyceraldehyde as a chiral precursor. Under optim
Prolinal dithioacetals: Highly efficient organocatalysts for the direct nitro-Michael additions in both organic and aqueous media
Mandal, Tanmay,Kuo, Wen,Su, Matthew,Bhowmick, Kartick,Zhao, John C.-G.
, p. 6597 - 6603 (2017/10/18)
Some novel prolinal dithioacetal derivatives have been synthesized and applied as the organocatalysts for the direct Michael addition of ketones and aldehydes to nitroalkenes. High enantioselectivities and diastereoselectivities have been obtained in both
