Cargando…

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

We present here a stereoselective tandem reaction based on the asymmetric conjugate addition of dialkylzinc reagents to unsaturated acylimidazoles followed by trapping of the intermediate zinc enolate with carbocations. The use of a chiral NHC ligand provides chiral zinc enolates in high enantiomeri...

Descripción completa

Detalles Bibliográficos
Autores principales:	Mudráková, Brigita, Marcia de Figueiredo, Renata, Campagne, Jean-Marc, Šebesta, Radovan
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	Beilstein-Institut 2023
Materias:	Full Research Paper
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10280057/ https://www.ncbi.nlm.nih.gov/pubmed/37346500 http://dx.doi.org/10.3762/bjoc.19.65

Ejemplares similares

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles
por: Kisszékelyi, Péter, et al.
Publicado: (2023)

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors
por: Schmid, Thibault E, et al.
Publicado: (2015)

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure
por: Vargová, Denisa, et al.
Publicado: (2018)

Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
por: Peng, Jiahuan, et al.
Publicado: (2013)

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors
por: Pichon, Delphine, et al.
Publicado: (2020)

Chemical reaction networks based on conjugate additions on β′-substituted Michael acceptors
por: Spitzbarth, Benjamin, et al.
Publicado: (2023)

Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans
por: Belmessieri, Dorine, et al.
Publicado: (2014)

Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives
por: Li, Zheng-Yi, et al.
Publicado: (2018)

Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole
por: Silm, Estelle, et al.
Publicado: (2022)

Caryolene-forming carbocation rearrangements
por: Nguyen, Quynh Nhu N, et al.
Publicado: (2013)

Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors
por: Rajić, Zrinka, et al.
Publicado: (2018)

Enantioselective Michael Addition of Water
por: Chen, Bi-Shuang, et al.
Publicado: (2015)

The cyclopropylcarbinyl route to γ-silyl carbocations
por: Creary, Xavier
Publicado: (2019)

Conjugative Stabilization versus Anchimeric Assistance in Carbocations
por: Shainyan, Bagrat A.
Publicado: (2022)

New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions
por: Klare, Helge, et al.
Publicado: (2014)

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins
por: Castán, Alejandro, et al.
Publicado: (2017)

A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
por: Vepreva, Anastasia, et al.
Publicado: (2022)

A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors
por: Nacca, Francesca Giulia, et al.
Publicado: (2020)

New advances in asymmetric organocatalysis
por: Šebesta, Radovan
Publicado: (2022)

Asymmetric Michael Addition Mediated by Chiral Ionic Liquids
por: Suzuki, Yumiko
Publicado: (2018)

Transient and intermediate carbocations in ruthenium tetroxide oxidation of saturated rings
por: Pedrón, Manuel, et al.
Publicado: (2019)

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates
por: Kisszékelyi, Péter, et al.
Publicado: (2022)

Catalyst-Free Formal Conjugate Addition/Aldol or Mannich Multicomponent Reactions of Mixed Aliphatic Organozinc Reagents, π-Electrophiles and Michael Acceptors
por: Pinaud, Marine, et al.
Publicado: (2023)

Michael Additions of Amines to Methyl Acrylates Promoted by Microwave Irradiation
por: Escalante, Jaime, et al.
Publicado: (2008)

Computational Study of the Addition of Methanethiol to 40+ Michael Acceptors as a Model for the Bioconjugation of Cysteines
por: Costa, Anna M., et al.
Publicado: (2021)

Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives
por: Han, Jianlin, et al.
Publicado: (2022)

Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective
por: Boyko, Yaroslav Dmitrievich, et al.
Publicado: (2017)

β-Hydroxy carbocation intermediates in solvolyses of di- and tetra-hydronaphthalene substrates
por: Kudavalli, Jaya S, et al.
Publicado: (2010)

Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
por: Kennedy, Sean H, et al.
Publicado: (2019)

Cu-catalyzed carboboration of acetylene with Michael acceptors
por: Cheng, Tairan, et al.
Publicado: (2022)

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor
por: El-Marrouki, Dalel, et al.
Publicado: (2020)

Rigidified Bis(sulfonyl)ethylenes as Effective Michael Acceptors for Asymmetric Catalysis: Application to the Enantioselective Synthesis of Quaternary Hydantoins
por: Villaescusa, Leire, et al.
Publicado: (2023)

Spontaneous Transition of Alkyl Carbocations to Unsaturated Vinyl-Type Carbocations in Organic Solutions
por: Stoyanov, Evgenii S., et al.
Publicado: (2023)

Photoredox radical conjugate addition of dithiane-2-carboxylate promoted by an iridium(iii) phenyl-tetrazole complex: a formal radical methylation of Michael acceptors
por: Gualandi, Andrea, et al.
Publicado: (2017)

Nucleophilicity of Glutathione: A Link to Michael Acceptor Reactivities
por: Mayer, Robert J., et al.
Publicado: (2019)

Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections
por: Strharsky, Tomas, et al.
Publicado: (2022)

Michael acceptor molecules in natural products and their mechanism of action
por: Liang, Song-Ting, et al.
Publicado: (2022)

Synergistic Catalysis of Tandem Michael Addition/Enantioselective Protonation Reactions by an Artificial Enzyme
por: Zhou, Zhi, et al.
Publicado: (2021)

Unlocking Asymmetric Michael Additions in an Archetypical Class I Aldolase by Directed Evolution
por: Kunzendorf, Andreas, et al.
Publicado: (2021)

Primary-tertiary diamine-catalyzed Michael addition of ketones to isatylidenemalononitrile derivatives
por: Kumar, Akshay, et al.
Publicado: (2014)

Cannot write session to /tmp/vufind_sessions/sess_29jltpbqoscuv6a1idg44e9h35