Cargando…

Reversal of Enantioselectivity in the Conjugate Addition Reaction of Cyclic Enones with the CuOTf/Azolium Catalytic System

Hydroxyamide-functionalized azolium salt (NHC•HI 4) was evaluated for dual enantioselective control in a Cu-catalyzed asymmetric conjugate addition (ACA) reaction. This investigation was based on our previously reported ACA reaction catalyzed using CuOTf combined with NHC•AgI complex 1. It was revea...

Descripción completa

Detalles Bibliográficos
Autores principales:	Nakano, Yuki, Shimizu, Satoki, Takeda, Chihiro, Sakaguchi, Satoshi
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	MDPI 2021
Materias:	Article
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8200092/ https://www.ncbi.nlm.nih.gov/pubmed/34199812 http://dx.doi.org/10.3390/molecules26113404

Ejemplares similares

Enantioselective Annulations for Dihydroquinolones by in Situ Generation of Azolium Enolates
por: Lee, Anna, et al.
Publicado: (2014)

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
por: Peters, Bram B. C., et al.
Publicado: (2020)

Enantioselective Cu(I)-catalyzed borylative cyclization of enone-tethered cyclohexadienones and mechanistic insights
por: Jadhav, Sandip B., et al.
Publicado: (2022)

Enantioselective Intermolecular [2+2] Photocycloaddition Reaction of Cyclic Enones and Its Application in a Synthesis of (−)-Grandisol
por: Poplata, Saner, et al.
Publicado: (2018)

Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones
por: Boylan, Amy, et al.
Publicado: (2021)

Acyl Donor Intermediates in N‐Heterocyclic Carbene Catalysis: Acyl Azolium or Azolium Enolate?
por: Biswas, Animesh, et al.
Publicado: (2021)

Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts
por: Wang, Qingqing, et al.
Publicado: (2017)

Catalytic enantioselective allene–anhydride approach to β,γ-unsaturated enones bearing an α-all-carbon-quarternary center
por: Yuan, Yuan, et al.
Publicado: (2020)

Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
por: Farley, Conner M., et al.
Publicado: (2018)

Catalytic Enantioselective Synthesis of α-Difunctionalized Cyclic Sulfones
por: Bowen, Eleanor, et al.
Publicado: (2022)

Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones
por: Boeser, Cornelia L., et al.
Publicado: (2015)

Squaramide-Catalyzed Enantioselective Michael Addition of Masked Acyl Cyanides to Substituted Enones
por: Yang, Kin S., et al.
Publicado: (2013)

Iron-Catalyzed Coupling of Alkenes and Enones: Sakurai–Michael-type Conjugate Addition of Catalytic Allyliron Nucleophiles
por: Scrivener, Sarah G., et al.
Publicado: (2023)

Electrophilic reactivities of cyclic enones and α,β-unsaturated lactones
por: Mayer, Robert J., et al.
Publicado: (2021)

Enantioselective Synthesis of Chiral Cyclopent‐2‐enones by Nickel‐Catalyzed Desymmetrization of Malonate Esters
por: Karad, Somnath Narayan, et al.
Publicado: (2018)

Construction of cyclic enones via gold-catalyzed oxygen transfer reactions
por: Liu, Leping, et al.
Publicado: (2011)

Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
por: Zuo, Xiao-Dong, et al.
Publicado: (2017)

Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Brønsted acids
por: Wang, Guo-Peng, et al.
Publicado: (2017)

Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
por: Zhou, Wei, et al.
Publicado: (2017)

(S)-2-(1-Hydroxyethyl)benzimidazolium dihydrogen phosphate
por: Xia, Rong
Publicado: (2009)

Crystal Engineering of Ionic Cocrystals Sustained by Azolium···Azole Heterosynthons
por: Rahmani, Maryam, et al.
Publicado: (2022)

A N,N′-dioxide/Mg(OTf)(2) complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates
por: Luo, Weiwei, et al.
Publicado: (2016)

Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups
por: Meng, Fanke, et al.
Publicado: (2016)

Synthesis and Structural Verification of an ArI(OTf)(2), NO(2)‐Ph‐I(OTf)(2)
por: Sharp‐Bucknall, Lachlan, et al.
Publicado: (2022)

Bi(OTf)(3) and SiO(2)-Bi(OTf)(3) as Effective Catalysts for the Ferrier Rearrangement#
por: Babu, J. Lokesh, et al.
Publicado: (2005)

Enantioselective direct Michael addition of cyanohydrin ether derivatives to enones catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase
por: Das, Saikat, et al.
Publicado: (2023)

Niobium Pentachloride Activation of Enone Derivatives: Diels- Alder and Conjugate Addition Products
por: Constantino, Mauricio Gomes, et al.
Publicado: (2002)

Regio- and Enantioselective Catalytic Monoepoxidation of Conjugated Dienes: Synthesis of Chiral Allylic cis-Epoxides
por: Jat, Jawahar L., et al.
Publicado: (2015)

Diastereoselective [2+2] Photocycloaddition of Chiral Cyclic Enones with Olefins in Aqueous Media Using Surfactants
por: Nishiyama, Yasuhiro, et al.
Publicado: (2013)

Intramolecular [2+2] Photocycloaddition of Cyclic Enones: Selectivity Control by Lewis Acids and Mechanistic Implications
por: Poplata, Saner, et al.
Publicado: (2019)

Stereoselective Iridium-N,P-Catalyzed Double Hydrogenation of Conjugated Enones to Saturated Alcohols
por: Peters, Bram B. C., et al.
Publicado: (2022)

Nitrene‐Mediated C−H Oxygenation: Catalytic Enantioselective Formation of Five‐Membered Cyclic Organic Carbonates
por: Nie, Xin, et al.
Publicado: (2022)

H‐Bonded Counterion‐Directed Catalysis: Enantioselective Gold(I)‐Catalyzed Addition to 2‐Alkynyl Enones as a Case Study
por: Martí, Àlex, et al.
Publicado: (2022)

A Mild Catalytic Oxidation System: FePcOTf/H(2)O(2) Applied for Cyclohexene Dihydroxylation
por: Zhou, Baocheng, et al.
Publicado: (2015)

Chicken Ovotransferrin Variants OTF(B) and OTF(C) Harboring Substitution of GAT (Asp) to AAT (Asn) in the Codon 500 and their Antimicrobial Activity
por: Kinoshita, Keiji, et al.
Publicado: (2016)

Hybrid Supramolecules for Azolium-Linked Cyclophane Immobilization and Conformation Study: Synthesis, Characterization, and Photocatalytic Degradation
por: Li, Yuan-Yuan, et al.
Publicado: (2019)

A Review on Generation and Reactivity of the N-Heterocyclic Carbene-Bound Alkynyl Acyl Azolium Intermediates
por: Dong, Ziyang, et al.
Publicado: (2022)

Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones
por: Gao, Zhenbo, et al.
Publicado: (2017)

Design and Synthesis of Novel Double-Ring Conjugated Enones as Potent Anti-rheumatoid Arthritis Agents
por: Zhou, Shiyang, et al.
Publicado: (2022)

Cu(OTf)(2)‐Mediated Cross‐Coupling of Nitriles and N‐Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products
por: Bell, Nicola L., et al.
Publicado: (2021)

Cannot write session to /tmp/vufind_sessions/sess_1ihojle17kace5frpe3girf915