4.5 Review

Enantioselective Dual Catalysis of N-Heterocyclic Carbene and Hydrogen-Bond Donor Organocatalysts

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Organo/Transition-Metal Combined Catalysis Rejuvenates Both in Asymmetric Synthesis

Dian-Feng Chen et al.

Summary: This article introduces the fundamental attributes of asymmetric organo/transition-metal combined catalysis (AOMC), explains how organocatalysts and transition-metal complexes collaborate, and discusses future opportunities in this field.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Asymmetric Carbene-Catalyzed Oxidation of Functionalized Aldimines as 1,4-Dipoles

Guanjie Wang et al.

Summary: Functionalized aldimines have been used as new 1,4-dipole precursors in carbene catalysis, leading to enantiodivergent organocatalysis for the synthesis of both (R)- and (S)- enantiomers of compounds with quaternary carbon centers. The key factors for controlling enantioselectivity were found to be hydrogen bond C-H...F interactions between catalyst and substrate. These new 1,4-dipoles can also react with isatin and its imines under carbene catalysis, producing spiro oxindoles with excellent enantiomeric ratios.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Carbene-Catalyzed Activation of Remote Nitrogen Atoms of (Benz)imidazole-Derived Aldimines for Enantioselective Synthesis of Heterocycles

Xing Yang et al.

Summary: This new mode of carbene-catalyzed reaction involves the activation of a nitrogen atom in a triaza-diene intermediate, leading to highly enantioselective reactions with activated ketones. The reaction pathway is supported by mechanistic studies and preliminary density function theory calculations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Kinetic Resolution of Aziridines Enabled by N-Heterocyclic Carbene/Copper Cooperative Catalysis: Carbene Dose-Controlled Chemo-Switchability

Zi-Jing Zhang et al.

Summary: The study developed an efficient KR and DyKAT method using N-heterocyclic carbene (NHC)/copper cooperative catalysis, resulting in highly enantioenriched derivatives and products with high structural diversity. Mechanistic studies indicated that NHC can regulate the catalytic activity of the copper catalyst, enabling the switch of chemical selectivity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Synthesis of Functionalized Dihydrocoumarins by NHC-Catalyzed [3+3] Annulation of Enals with 2-Substituted Naphthoquinones

Sayan Shee et al.

Summary: This study describes a method for the facile synthesis of functionalized dihydrocoumarins catalyzed by N-heterocyclic carbene (NHC), in which initially formed NHC-homoenolates undergo a specific reaction pathway to yield the products. Preliminary studies indicate that the homoenolate pathway may be more favorable than other intermediates for product formation.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

NHC-Catalyzed Desymmetrization of N-Aryl Maleimides Leading to the Atroposelective Synthesis of N-Aryl Succinimides

Soumen Barik et al.

Summary: This study describes the atroposelective synthesis of N-aryl succinimides with axially chiral C-N bonds catalyzed by N-heterocyclic carbenes, achieving good yields and ee values. Preliminary investigations were also conducted on the rotation barrier for the C-N bond, temperature dependence, and detailed DFT studies on the mechanism.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

A Bifunctional N-Heterocyclic Carbene as a Noncovalent Organocatalyst for Enantioselective Aza-Michael Addition Reactions

Fangfang Guo et al.

Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.

ACS CATALYSIS (2021)

Review Chemistry, Multidisciplinary

Recent advances in the chemistry and applications of N-heterocyclic carbenes

Peter Bellotti et al.

Summary: N-Heterocyclic carbenes have attracted significant interest due to their versatility, modularity and strong coordinating properties, leading to a rapid increase in utilization across various fields in the past decade. Future directions and recent developments in the field are also highlighted in this review.

NATURE REVIEWS CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

Yonggui Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Gold and Carbene Relay Catalytic Enantioselective Cycloisomerization/Cyclization Reactions of Ynamides and Enals

Liejin Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

N-HeterocyclicCarbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

Xingkuan Chen et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction

Shitian Zhuo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Physical

The Combination of Lewis Acid with N-Heterocyclic Carbene (NHC) Catalysis

Qianfa Jia et al.

CATALYSTS (2019)

Review Chemistry, Multidisciplinary

Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates

Samson Afewerki et al.

TOPICS IN CURRENT CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Highly Enantioselective [5+2] Annulations through Cooperative N-Heterocyclic Carbene (NHC) Organocatalysis and Palladium Catalysis

Santanu Singha et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Switching Reaction Pathways by Cooperative Catalysis of N-Heterocyclic Carbene and Lewis Acids

Wang Leming et al.

ACTA CHIMICA SINICA (2018)

Article Chemistry, Organic

Synthesis of 3-Formylbenzenesulfonyl Chloride Derivativesv

Xuefei Bao et al.

SYNTHESIS-STUTTGART (2017)

Article Multidisciplinary Sciences

A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization

Xingkuan Chen et al.

NATURE COMMUNICATIONS (2017)

Article Chemistry, Applied

A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters

Kathleen J. R. Murauski et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Review Chemistry, Multidisciplinary

Cooperative Catalysis and Activation with N-Heterocyclic Carbenes

Michael H. Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Cooperative N-Heterocyclic Carbene/Palladium-Catalyzed Enantioselective Umpolung Annulations

Chang Guo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Multidisciplinary

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes

Darrin M. Flanigan et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Multidisciplinary

Enantioselective β-Protonation by a Cooperative Catalysis Strategy

Michael H. Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Review Chemistry, Organic

Combined Asymmetric Aminocatalysis and Carbene Catalysis

Jing Gu et al.

SYNTHESIS-STUTTGART (2015)

Article Chemistry, Multidisciplinary

Intermolecular Dynamic Kinetic Resolution Cooperatively Catalyzed by an N-Heterocyclic Carbene and a Lewis Acid

Zijun Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Multidisciplinary

Asymmetric Organocatalysis Combined with Metal Catalysis: Concept, Proof of Concept, and Beyond

Dian-Feng Chen et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid

Srikrishna Bera et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Dual Catalysis Sees the Light: Combining Photoredox with Organo-, Acid, and Transition-Metal Catalysis

Matthew N. Hopkinson et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Article Multidisciplinary Sciences

Metal and carbene organocatalytic relay activation of alkynes for stereoselective reactions

Kayambu Namitharan et al.

NATURE COMMUNICATIONS (2014)

Article Chemistry, Multidisciplinary

Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N-Heterocyclic-Carbene/Thiourea/Tertiary-Amine Multicatalysis

Zhichao Jin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis

Adel M. ElSohly et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Enantioselective N-Heterocyclic Carbene Catalyzed Aza-Benzoin Reaction of Enals with Activated Ketimines

Li-Hui Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

Combining transition metal catalysis and organocatalysis - an update

Zhenting Du et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Multidisciplinary

An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones

Julien Dugal-Tessier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Review Chemistry, Multidisciplinary

Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals

Javier Magano et al.

CHEMICAL REVIEWS (2011)

Review Chemistry, Multidisciplinary

Dual Activation in N-Heterocyclic Carbene-organocatalysis

Keiichi Hirano et al.

CHEMISTRY LETTERS (2011)

Article Multidisciplinary Sciences

Enantioselective benzoin condensation catalyzed by bifunctional N-heterocyclic carbenes

Huang XueLiang et al.

CHINESE SCIENCE BULLETIN (2010)

Article Chemistry, Multidisciplinary

Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates

Benoit Cardinal-David et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactams

Dustin E. A. Raup et al.

NATURE CHEMISTRY (2010)

Article Chemistry, Organic

Synthesis of Chiral Bifunctional (Thio)Urea N-Heterocyclic Carbenes

Jonathan P. Brand et al.

SYNLETT (2010)

Article Chemistry, Inorganic & Nuclear

Synthesis of enantiopure triazolium salts from pyroglutamic acid and their evaluation in the benzoin condensation

Dieter Enders et al.

TETRAHEDRON-ASYMMETRY (2008)

Review Chemistry, Multidisciplinary

Organocatalysis by N-heterocyclic, carbenes

Dieter Enders et al.

CHEMICAL REVIEWS (2007)

Article Chemistry, Multidisciplinary

Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination

AE Mattson et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Review Chemistry, Applied

Recent progress in chiral Bronsted acid catalysis

Takahiko Akiyama et al.

ADVANCED SYNTHESIS & CATALYSIS (2006)

Article Chemistry, Inorganic & Nuclear

New bidentate alkoxy-NHC ligands for enantioselective copper-catalysed conjugate addition

H Clavier et al.

TETRAHEDRON-ASYMMETRY (2005)

Article Chemistry, Multidisciplinary

Thiazolylaianine-derived catalysts for enantioselective intermolecular aldehyde-imine cross-couplings

SM Mennen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Multidisciplinary

A peptide-catalyzed asymmetric Stetter reaction

SM Mennen et al.

CHEMICAL COMMUNICATIONS (2005)