1301133-89-0Relevant academic research and scientific papers
Novel binaphthyl and biphenyl α- and β-amino acids and esters: organocatalysis of asymmetric Diels-Alder reactions. A combined synthetic and computational study
Bulman Page, Philip C.,Kinsey, Francesca S.,Chan, Yohan,Strutt, Ian R.,Slawin, Alexandra M. Z.,Jones, Garth A.
, p. 7400 - 7416 (2018)
Asymmetric catalysis of the Diels-Alder reaction between cyclopentadiene and cinnamaldehydes has been studied using as catalysts a range of novel α- and β-aminoacids and aminoesters with binaphthyl and biphenyl backbones, providing enantioselectivities of
Non-Covalently Immobilized Chiral Imidazolidinone on Sulfated-Chitin: Reusable Heterogeneous Organocatalysts for Asymmetric Diels-Alder Reaction
Watanabe, Mirai,Sakai, Takuya,Oka, Marina,Makinose, Yuki,Miyazaki, Hidetoshi,Iida, Hiroki
supporting information, p. 255 - 260 (2019/12/11)
A heterogeneous chiral imidazolodinone catalyst was synthesized by immobilization on a sulfated chitin through non-covalent ionic interactions. The chitin-based organocatalyst promoted the asymmetric Diels-Alder reaction with high enantioselectivity under heterogeneous conditions and was successfully reused multiple times without apparent loss of catalytic activity and enantioselectivity.
Enantioselective Organocatalytic Enamine C?H Oxidation/Diels- Alder Reaction
D?ambaski, Zdravko,Tzaras, Dimitrios-Ioannis,Lee, Sunggi,Kokotos, Christoforos G.,Bondzic, Bojan P.
supporting information, p. 1792 - 1797 (2019/02/25)
α,β-unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single-electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels-Alder reaction. This enantioselective one-pot transformation represents the first example of saturated aldehydes being used in domino Diels-Alder reaction processes and demonstrates the power of this protocol for construction of stereo-defined chiral compounds and building blocks. (Figure presented.).
Chiral GAP catalysts of phosphonylated imidazolidinones and their applications in asymmetric Diels-Alder and Friedel-Crafts reactions
Qiao, Shuo,Mo, Junming,Wilcox, Cody B.,Jiang, Bo,Li, Guigen
, p. 1718 - 1724 (2017/02/23)
The design and synthesis of recyclable imidazolidinone catalysts using GAP chemistry/technique was described. Their applications in asymmetric Diels-Alder and Friedel-Crafts reactions with α,β-unsaturated aldehydes resulted in excellent yields and higher enantioselectivities than previous processes. As recyclable small molecular catalysts, phosphonylated imidazolidinones can be recovered and reused for up to three runs without costing significant decrease in catalytic activity.
Pentaerythritol-supported chiral imidazolone and preparation method as well as use thereof
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Paragraph 0024, (2016/10/08)
The invention relates to pentaerythritol-supported chiral imidazolone. The structure of the pentaerythritol-supported chiral imidazolone is shown in the description. Chiral imidazolone is supported on pentaerythritol to obtain a novel pentaerythritol-supp
Caveat in the stereochemical outcome of the organocatalytic Diels-Alder reaction in PEG-400
Anitha, Pantapalli M.,Mainkar, Prathama S.,Kallepu, Shivakrishna,Babu, V. S. Phani,Reddy, Cirandur Suresh,Chandrasekhar, Srivari
, p. 76132 - 76136 (2016/09/04)
The organocatalytic Diels-Alder reaction in non-conventional solvent (PEG-400) has yielded cycloaddition products with diastereoselectivities hitherto not reported in detail using classical reaction conditions.
New insights into the asymmetric Diels-Alder reaction: The endo- and S-selective retro-Diels-Alder reaction
Li, Na,Liang, Xianrui,Su, Weike
, p. 106234 - 106238 (2015/12/30)
The endo- and S-selective retro-Diels-Alder reactions in an imidazolethione-catalyzed asymmetric Diels-Alder reaction were verified and investigated, and account for the low ee values in a CH3CN-H2O catalytic system. This reverse pro
Improving catalyst activity in secondary amine catalysed transformations
Brazier, John B.,Gibbs, Timothy J. K.,Rowley, Julian H.,Samulis, Leopold,Yau, Sze Chak,Kennedy, Alan R.,Platts, James A.,Tomkinson, Nicholas C. O.
supporting information, p. 133 - 141 (2015/02/05)
The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of l-phenylalanine N-methyl amide with acetophenone derivatives results in a series of imidazolidinones whose sa
Recyclable tetraarylphosphonium supported chiral imidazolidin-4-one organocatalyst for Diels-Alder reactions
Lin, Zihan,Chen, Zuxing,Yang, Guichun,Lu, Cuifen
, p. 1 - 5 (2013/05/09)
The tetraarylphosphonium supported chiral imidazolidin-4-ones were synthesized and used to catalyze the Diels-Alder reactions of cyclopentadiene and α,β-unsaturated aldehydes. High enantiomeric excesses and good yields were obtained, and catalyst recyclin
The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis
Gould, Eoin,Lebl, Tomas,Slawin, Alexandra M. Z.,Reid, Mark,Davies, Tony,Smith, Andrew D.
, p. 7877 - 7892 (2013/11/19)
Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organocatalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of β-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.
