154317-89-2Relevant academic research and scientific papers
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
supporting information, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
Asymmetric Synthesis of α-Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis
Capaccio, Vito,Sicignano, Marina,Rodríguez, Ricardo I.,Della Sala, Giorgio,Alemán, José
supporting information, p. 219 - 223 (2019/12/30)
The first asymmetric α-trifluoromethylthiolation of 2-substituted isoxazolidin-5-ones was developed using Maruoka type N-spiro ammonium catalysts under phase-transfer conditions. The resulting products, containing a trifluoromethylthiolated quaternary chiral carbon, were obtained in moderate to good yields and up to 98:2 enantiomeric ratio. Moreover, the easy N-O bond cleavage provided access to undescribed α-trifluoromethylthio-β2,2-amino acids, with promising applications in biochemistry and medicinal chemistry.
Di- and triarylmethylium ions as probes for the ambident reactivities of carbanions derived from 5-benzylated Meldrum's acid
Chen, Xi,Tan, Yue,Berionni, Guillaume,Ofial, Armin R.,Mayr, Herbert
, p. 11069 - 11077 (2014/10/15)
The kinetics of the reactions of carbocations with carbanions 1 derived from 5-benzyl-substituted Meldrum's acids 1-H (Meldrum's acid=2,2-dimethyl-1,3- dioxane-4,6-dione) were investigated by UV/Vis spectroscopic methods. Benzhydryl cations Ar2CH+ added exclusively to C-5 of the Meldrum's acid moiety. As the second-order rate constants (kC) of these reactions in DMSO followed the linear free-energy relationship lg k=s N(N+E), the nucleophile-specific reactivity parameters N and s N for the carbanions 1 could be determined. In contrast, trityl cations Ar3C+ reacted differently. While tritylium ions of low electrophilicity (E-2) reacted with 1 through rate-determining β-hydride abstraction, more Lewis acidic tritylium ions initially reacted at the carbonyl oxygen of 1 to form trityl enolates, which subsequently reionized and eventually yielded triarylmethanes and 5-benzylidene Meldrum's acids by hydride transfer.
NOVEL MALONIC ACID SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL USE THEREOF
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Page/Page column 89, (2010/04/25)
The present invention provides a novel compound having an agonist action at AT2 receptor and expected as a pharmaceutical product, and also provides a method of treating or preventing various diseases. The novel sulfonyl malonamide derivative,
Lewis base-promoted hydrosilylation of cyclic malonates: Synthesis of β-substituted aldehydes and γ-substituted amines
Frost, Christopher G.,Hartley, Benjamin C.
supporting information; experimental part, p. 3599 - 3602 (2009/09/05)
The Lewis base-promoted hydrosilylation of cyclic malonates provides a convenient synthesis of β-substituted aldehydes. No over-reduction to the primary alcohol is observed as the aldehyde functionality is protected until a subsequent hydrolysis step. The
Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: Diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals
Ramachary, Dhevalapally B.,Venkaiah, Chintalapudi,Reddy, Y. Vijayendar,Kishor, Mamillapalli
supporting information; scheme or table, p. 2053 - 2062 (2009/09/05)
In this paper we describe new multi-catalysis cascade (MCC) reactions for the one-pot synthesis of highly functionalized non-symmetrical malonates. These metal-free reactions are either five-step (olefination/hydrogenation/alkylation/ ketenization/esterif
Tandem molybdenum catalyzed hydrosilylations: An expedient synthesis of β-aryl aldehydes
Frost, Christopher G.,Hartley, Benjamin C.
, p. 4259 - 4261 (2008/02/12)
The synthesis of β-aryl aldehydes utilizing a tandem molybdenum catalyzed hydrosilylation is described. This new functional group interconversion provides an efficient method for the two-carbon homologation of aryl aldehydes.
A novel and green protocol for two-carbon homologation: A direct amino acid/K2CO3-catalyzed four-component reaction of aldehydes, active methylenes, Hantzsch esters and alkyl halides
Ramachary, Dhevalapally B.,Kishor,Ramakumar
, p. 651 - 656 (2007/10/03)
A novel and green approach for the two-carbon homologation of aldehydes using amino acid catalysis has been developed and further extended to the generation of pharmaceutically active cyano-esters via four-component reactions in one-pot.
