4.8 Article

Asymmetric C-H Activation for the Synthesis of P- and Axially Chiral Biaryl Phosphine Oxides by an Achiral Cp*Ir Catalyst with Chiral Carboxylic Amide

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Ruthenium(II)/Chiral Carboxylic Acid Catalyzed Enantioselective C-H Functionalization of Sulfoximines

Long-Tao Huang et al.

Summary: The study presents ruthenium(II)-catalyzed enantioselective C-H functionalization reactions of sulfoximines with sulfoxonium ylides. The combination of [RuCl2(p-cymene)](2) and a pseudo-C-2-symmetric binaphthyl monocarboxylic acid yielded S-chiral products in 76:24 to 92:8 er.

SYNTHESIS-STUTTGART (2022)

Review Chemistry, Multidisciplinary

Chiral Cyclopentadienyl Ligands: Design, Syntheses, and Applications in Asymmetric Catalysis

Josep Mas-Rosello et al.

Summary: The development of new chiral ligands is crucial for stereocontrol in metal-catalyzed reactions, especially with the increasing demand for bioactive molecules as single enantiomers. The successful application of Cp-X ligands in metal-catalyzed transformations allows access to valuable chiral molecules, with critical comparisons of existing ligand families and discussion of future research directions for further enhancing their performance and application in enantioselective catalysis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Chiral Catalysts for Pd0-Catalyzed Enantioselective C-H Activation

Oleksandr Vyhivskyi et al.

Summary: Processes involving transition-metal catalysis have become a major part of synthetic chemists' toolbox in recent decades. The focus has shifted from cross-coupling reactions to C-H bond functionalization, with constant progress leading to discovery of enantioselective methods. The review discusses enantioselective Pd-0-catalyzed C-H activation, highlighting the importance of different chiral ligands and catalysts in enabling these transformations.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Multidisciplinary

Cobalt-Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of P-Stereogenic Compounds

Zeng-Hua Wu et al.

Summary: Utilizing the pyridinyl moiety as the coordinating group in cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides can lead to the efficient synthesis of tertiary phosphine oxides with high yields and high enantiomeric excess, along with broad functional-group tolerance. Mechanistic studies reveal that (R)-secondary phosphine oxides preferentially interact with the cobalt catalysts to produce P-stereogenic compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation

Qiang Dai et al.

Summary: This study successfully achieved the kinetic resolution of rac-secondary phosphine oxides via enantioselective P-benzylation catalysis, delivering both tert- and sec-phosphine oxides in good yield and excellent enantiopurity. The synthetic utilities were further demonstrated by the facile preparation of valuable P-chiral compounds, precursors of bidentate ligands, and transition metal complexes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Iridium-Catalyzed Enantioselective C-H Borylation of Diarylphosphinates

Shu-Yong Song et al.

Summary: This study presents a novel method for the synthesis of P-stereogenic phosphorus compounds through phosphinate-directed iridium-catalyzed reactions, with high yields and good enantioselectivities. The borylated products synthesized can be used for the preparation of precursors for chiral phosphine ligands, showing potential industrial applications.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Oxygen-Linked Cyclopentadienyl Rhodium(III) Complexes-Catalyzed Asymmetric C-H Arylation of Benzo[h]quinolines with 1-Diazonaphthoquinones

Chongqing Pan et al.

Summary: The development of tunable chiral cyclopentadienyl ligands bearing oxygen linkers has addressed the limitations of C-linked Cp ligands and their synthetic challenges, resulting in efficient catalysts for C-H arylation reactions. These catalysts have shown excellent yields and enantioselectivity in the synthesis of axially chiral heterobiaryls.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex

Chuanyong Wang et al.

Summary: The first highly enantioselective catalytic synthesis of P-stereogenic secondary phosphine-boranes was achieved using a newly developed unsymmetric bisphosphine pincer-nickel complex. Various P-stereogenic secondary phosphine-boranes were obtained in good yields with high enantioselectivity and diastereoselectivity. Subsequent alkylation upon P-C bond formation provided a practical way to access P-chiral compounds with diverse functional groups.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid

Tao Zhou et al.

Summary: An undeveloped Ru(II)-catalyzed enantioselective C-H functionalization involving an enantiodetermining C-H cleavage step has been described in this study. Using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, a broad range of sulfur-stereogenic sulfoximines were synthesized in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution. Furthermore, the resolution products can be easily transformed into chiral sulfoxides and key intermediates for kinase inhibitors.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Physical

Development of Pseudo-C2-symmetric Chiral Binaphthyl Monocarboxylic Acids for Enantioselective C(sp3)-H Functionalization Reactions under Rh(III) Catalysis

Yoshimi Kato et al.

Summary: By introducing pseudo-C2 symmetric tunable chiral carboxylic acids, the study achieved enantioselective C(sp(3))-H amidation reactions of substrates such as 2-alkylpyridines, improving the chiral selectivity towards the substrates.

ACS CATALYSIS (2021)

Article Chemistry, Physical

Chiral Carboxylic Acid Assisted Enantioselective C-H Activation with Achiral CpxMIII (M = Co, Rh, Ir) Catalysts

Tatsuhiko Yoshino et al.

Summary: Enantioselective C-H functionalization is a powerful tool for synthesizing chiral molecules. The combination of high-valent group 9 metals with achiral Cp-x ligands and chiral carboxylic acids has shown promise in enabling selective cleavage and functionalization of enantiotopic C-H bonds. This Perspective provides a detailed summary of the background, catalyst design, applied reactions, and future directions in this field.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Twofold C-H Activation-Based Enantio- and Diastereoselective C-H Arylation Using Diarylacetylenes as Rare Arylating Reagents

Panjie Hu et al.

Summary: A novel method for the construction of biaryls with central and axial chirality through rhodium-catalyzed 1:2 coupling of diarylphosphinic amides and diarylacetylenes has been reported. This new method shows better chemoselectivity compared to previously explored Miura-Satoh type 1:2 coupling, and proceeds under mild conditions using a rare arylating reagent.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Rapid Synthesis of Chiral 1,2-Bisphosphine Derivatives through Copper(I)-Catalyzed Asymmetric Conjugate Hydrophosphination

Yue Wen-Jun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Diverse Approaches for Enantioselective C-H Functionalization Reactions Using Group 9 CpxMIII Catalysts

Tatsuhiko Yoshino et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Enantioselective C-H Functionalization via Chiral Transient Directing Group Strategies

Gang Liao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Construction of P-Chiral Alkenylphosphine Oxides through Highly Chemo-, Regio-, and Enantioselective Hydrophosphinylation of Alkynes

Qiang Dai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Chiral Bicyclo[2.2.2]octane-Fused CpRh Complexes: Synthesis and Potential Use in Asymmetric C-H Activation

Guozhu Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Designing a Planar Chiral Rhodium Indenyl Catalyst for Regio- and Enantioselective Allylic C-H Amidation

Caitlin M. B. Farr et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Functionalizations of C-H Bonds by Chiral Iridium Complexes

Lukasz Wozniak et al.

CHEMICAL REVIEWS (2020)

Article Chemistry, Multidisciplinary

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

Yan-Bo Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides

Ren-Yi Zhu et al.

ACTA CHIMICA SINICA (2020)

Article Chemistry, Organic

Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Quinone Monoketals

Guijiu Sun et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Asymmetric construction of quaternary α-nitro amides by palladium-catalyzed C(sp3)-H arylation

Wei-Xin Kong et al.

CHEMICAL COMMUNICATIONS (2020)

Review Chemistry, Multidisciplinary

Enantioselective C-H Activation with Earth-Abundant 3d Transition Metals

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Inorganic & Nuclear

Pd-Catalyzed Asymmetric C-H Bond Activation for the Synthesis of P-Stereogenic Dibenzophospholes

Zhen Li et al.

ORGANOMETALLICS (2019)

Review Chemistry, Physical

Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization

Johannes Diesel et al.

ACS CATALYSIS (2019)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Methylene C(sp3)-H Amidation of 8-Alkylquinolines Using a Cp*RhIII/Chiral Carboxylic Acid System

Seiya Fukagawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Asymmetric Allylation of Secondary Phosphine Oxides

Xu-Teng Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed PIII-Directed ortho-C-H Borylation of Arylphosphines

Jian Wen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System

Seiya Fukagawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Multidisciplinary Sciences

Enantioselective C(sp(3))-H bond activation by chiral transition metal catalysts

Tyler G. Saint-Denis et al.

SCIENCE (2018)

Article Chemistry, Multidisciplinary

Chiral Carboxylic Acid Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C-H Functionalization

Luqing Lin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Access to P- and Axially Chiral Biaryl Phosphine Oxides by Enantioselective (CpIrIII)-Ir-x-Catalyzed C-H Arylations

Yun-Suk Jang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Chiral-at-Sulfur 1,2-Benzothiazines by CpxRhIII-Catalyzed C-H Functionalization of Sulfoximines

Yang Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective Cobalt(III)-Catalyzed C-H Activation Enabled by Chiral Carboxylic Acid Cooperation

Fabio Pesciaioli et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Enantiotopic C-HActivation Enables Access to P-Chiral Cyclic Phosphinamides

Yang Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Transformations Involving C-H Bond Cleavage by Transition-Metal Complexes

Christopher G. Newton et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Rhodium(I)-Catalyzed Tertiary Phosphine Directed C-H Arylation: Rapid Construction of Ligand Libraries

Xiaodong Qiu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Spiropyrazolones by Rhodium-Catalyzed C(sp2)-H Functionalization/Annulation Reactions

Jun Zheng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

General Enantioselective C-H Activation with Efficiently Tunable Cyclopentadienyl Ligands

Zhi-Jun Jia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization

De-Wei Gao et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Article Chemistry, Multidisciplinary

Design and Synthesis of Novel Chiral Dirhodium(II) Carboxylate Complexes for Asymmetric Cyclopropanation Reactions

Frady G. Adly et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Review Chemistry, Multidisciplinary

Asymmetric Catalysis Powered by Chiral Cyclopentadienyl Ligands

Christopher G. Newton et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes

Michael Dieckmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Enantioselective CH Arylation for the Synthesis of P-Stereogenic Compounds

Zi-Qi Lin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed Enantioselective Synthesis of P-Stereogenic Phosphinamides via Desymmetric C-H Arylation

Zhi-Jun Du et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Chiral Cp-Rhodium(III)-Catalyzed Asymmetric Hydroarylations of 1,1-Disubstituted Alkenes

Baihua Ye et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of Isoindolones by Chiral Cyclopentadienyl-Rhodium(III)-Catalyzed C-H Functionalizations

Baihua Ye et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Iridium(III)-Catalyzed C-H Amidation of Arylphosphoryls Leading to a P-Stereogenic Center

Donghyeon Gwon et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Review Chemistry, Multidisciplinary

Recent development of direct asymmetric functionalization of inert C-H bonds

Chao Zheng et al.

RSC ADVANCES (2014)

Article Chemistry, Multidisciplinary

Pyridine-Directed Palladium-Catalyzed Phosphonation of C(sp2)-H Bonds

Changkun Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Organic

Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes

Yan-Chao Shi et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Asymmetric C(sp2)-H Activation

Joanna Wencel-Delord et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Chemistry, Multidisciplinary

A Tunable Class of Chiral Cp Ligands for Enantioselective Rhodium(III)-Catalyzed C-H Allylations of Benzamides

Baihua Ye et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed Phosphorylation of Aryl C-H Bonds

Chen-Guo Feng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

On the Interpretation of Deuterium Kinetic Isotope Effects in C?H Bond Functionalizations by Transition-Metal Complexes

Eric M. Simmons et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles via Enantioselective C-H Bond Functionalization

Ryo Shintani et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Inorganic & Nuclear

Recent developments in the asymmetric synthesis of P-chiral phosphorus compounds

Oleg I. Kolodiazhnyi

TETRAHEDRON-ASYMMETRY (2012)

Article Chemistry, Multidisciplinary

Fused Indolines by Palladium-Catalyzed Asymmetric C-C Coupling Involving an Unactivated Methylene Group

Masafumi Nakanishi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp(3))-H activation/cyclisation

Saithalavi Anas et al.

CHEMICAL COMMUNICATIONS (2011)

Article Chemistry, Organic

Palladium-Catalyzed Synthesis of Dibenzophosphole Oxides via Intramolecular Dehydrogenative Cyclization

Yoichiro Kuninobu et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Catalytic enantioselective synthesis of P-stereogenic compounds

James Stephen Harvey et al.

CHEMICAL COMMUNICATIONS (2010)

Review Chemistry, Multidisciplinary

Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Pathway

David Lapointe et al.

CHEMISTRY LETTERS (2010)

Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed Enantioselective C-H Olefination of Diphenylacetic Acids

Bing-Feng Shi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Enantioselective Palladium-Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters

Martin R. Albicker et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Chemistry, Multidisciplinary

Development of Ruthenium Catalysts for the Enantioselective Synthesis of P-Stereogenic Phosphines via Nucleophilic Phosphido Intermediates

Vincent S. Chan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Pd-II-catalyzed enantioselective activation of C(sp(2))-H and C(sp(3))-H bonds using monoprotected amino acids as chiral ligands

Bing-Feng Shi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Article Chemistry, Multidisciplinary

Catalytic asymmetric synthesis of chiral phosphanes

David S. Glueck

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Article Chemistry, Multidisciplinary

Pd(II)-catalyzed cross-coupling of sp3 C-H bonds with sp2 and sp3 boronic acids using air as the oxidant

Dong-Hui Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Synthesis of β-, γ-, and δ-Lactams via Pd(II)-Catalyzed C-H Activation Reactions

Masayuki Wasa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines

Vincent S. Chan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Palladium-catalyzed asymmetric phosphination. Scope, mechanism, and origin of enantioselectivity

Natalia F. Blank et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Review Chemistry, Inorganic & Nuclear

Preparation of optically pure P-stereogenic trivalent phosphorus compounds

Arnald Grabulosa et al.

COORDINATION CHEMISTRY REVIEWS (2007)

Article Chemistry, Multidisciplinary

Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex

VS Chan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Platinum-catalyzed asymmetric alkylation of secondary phosphines: Enantioselective synthesis of P-stereogenic phosphines

C Scriban et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Palladium-catalyzed asymmetric phosphination: Enantioselective synthesis of a P-chirogenic phosphine

JR Moncarz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)