☆ 4.8 Article

Synthesis of Sulfur-Stereogenic Sulfoximines via Co(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective C-H Amidation

ACS CATALYSIS (2022)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Multidisciplinary

Cobalt/Salox-Catalyzed Enantioselective C-H Functionalization of Arylphosphinamides

Qi-Jun Yao et al.

Summary: This study reports an unprecedented enantioselective C-H functionalization enabled by a simple cobalt/salicyloxazoline (Salox) catalysis. Chiral Salox ligands can be easily prepared in one step and used for the synthesis of various P-stereogenic compounds with high yields and excellent enantioselectivities. The isolation and characterization of several intermediates provide insights into the mechanism of active catalytic cobalt species generation, the action of Salox ligands, and the mode of stereocontrol.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Cobalt(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective Synthesis of Benzothiadiazine-1-oxides via C-H Activation

Yuki Hirata et al.

Summary: In this study, the combination of an achiral cobalt(III) catalyst and a pseudo-C-2-symmetric H-8-binaphthyl chiral carboxylic acid was utilized for the asymmetric synthesis of benzothiadiazine-1-oxides containing a chiral sulfur center. The optimized protocol achieved high enantioselectivity and allowed for the synthesis of benzothiadiazine-1-oxides with various functional groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Organic

Synthesis of P- and S-Stereogenic Compounds via Enantioselective C-H Functionalization

Pu-Fan Qian et al.

Summary: Transition metal-catalyzed enantioselective C-H functionalization is an important strategy for synthesizing various chiral molecules. This review summarizes the development and applications of different catalytic systems in achieving this strategy.

SYNTHESIS-STUTTGART (2022)

添加到收藏夹

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)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Medicinal

Application of sulfoximines in medicinal chemistry from 2013 to 2020

Yu Han et al.

Summary: Interest in sulfoximine chemistry has increased in recent years, with several sulfoximine-containing drugs entering clinical trials. However, limited experience in physicochemical and in vitro parameters of sulfoximines hampers their routine application in drug discovery. This review aims to provide support for the addition of sulfoximine components in medicinal chemists' toolbox.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation

Yan-Hua Liu et al.

Summary: The study reports a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by tailor-made amino acid ligands. A novel noncovalent interaction was found critical for the chiral induction, resulting in high yields and excellent enantioselectivities of C2-alkylated indoles. DFT calculations revealed the reaction mechanism and origins of chiral induction in the stereodetermining alkene insertion step.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Physical

Access to S-Stereogenic Free Sulfoximines via Bifunctional Phosphonium Salt-Catalyzed Desymmetrization of Bisphenols

Siqiang Fang et al.

Summary: The study presents an efficient and practical protocol for the direct enantioenrichment of free N-H sulfoximines. The method shows broad tolerability in desymmetrization and can easily be transformed into other classes of active sulfur-stereogenic compounds. Insights from mechanistic studies suggest a desymmetrization/KR synergic process with hydrogen-bonding interactions playing a key role in successful stereocontrol.

ACS CATALYSIS (2021)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Multidisciplinary

2-(Pyridin-2-yl)isopropyl (PIP) Amine: An Enabling Directing Group for Divergent and Asymmetric Functionalization of Unactivated Methylene C(sp3)-H Bonds

Qi Zhang et al.

Summary: The research focuses on the application of directed group (DG) assistance to address reactivity and selectivity challenges in C(sp(3))-H activation, achieving significant progress with the development of strongly coordinating bidentate DG and weakly coordinating monodentate DG strategies. The use of a novel strongly coordinating bidentate 2-(pyridine-yl)isopropyl (PIP) amine DG enabled divergent functionalization of unactivated beta-methylene C(sp(3))-H bonds, facilitating a series of important reactions.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Chiral Spirolactams via Sequential C-H Olefination/Asymmetric [4+1] Spirocyclization under a Simple CoII/Chiral Spiro Phosphoric Acid Binary System

Wen-Kui Yuan et al.

Summary: An unprecedented enantioselective synthesis of spiro-gamma-lactams was achieved using a simple Co-II/chiral spiro phosphoric acid binary system, resulting in high levels of enantioselectivity. Additionally, a concise synthesis of an aldose reductase inhibitor was successfully carried out under this system.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines

Yu Tang et al.

Summary: This study reports the synthesis of chiral sulfoximines through desymmetrizing N-oxidation, with the introduction of a directing group to enhance enantioinduction. Peptides with different C-terminal protecting groups were found to give opposite enantiomers of the product, suggesting a potential binding model to explain this phenomenon.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ii)-MPAA catalyzed C-H arylation and olefination

Kallol Mukherjee et al.

Summary: A direct Pd(ii)-catalyzed kinetic resolution of heteroaryl-enabled sulfoximines through an ortho-C-H alkenylation/arylation of arenes has been developed, providing access to a wide range of enantiomerically enriched unreacted aryl-pyridyl-sulfoximine precursors and C(aryl)-H alkenylation/arylation products in good yields with high enantioselectivity. The coordination of the directing group, ligand effect, geometry constraints, and the transient six-membered concerted-metalation-deprotonation species dictate the stereoselectivity, which is validated by DFT studies.

CHEMICAL SCIENCE (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Sulfur stereogenic centers in transition-metal-catalyzed asymmetric C-H functionalization: generation and utilization

Wentan Liu et al.

Summary: Transition-metal-catalyzed enantioselective C-H functionalization is a powerful tool for synthesizing enantioenriched compounds, with sulfur-based functionalities playing a key role. Recent advances have focused on utilizing sulfur functional groups and chiral sulfoxides to achieve stereoselective C-H functionalization.

CHEMICAL SCIENCE (2021)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Multidisciplinary

Modern Stereoselective Synthesis of Chiral Sulfinyl Compounds

Elzbieta Wojaczynska et al.

CHEMICAL REVIEWS (2020)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Medicinal

Sulfoximines as Rising Stars in Modern Drug Discovery? Current Status and Perspective on an Emerging Functional Group in Medicinal Chemistry

Patrick Maeder et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Organic

Cp*Co(III)/MPAA-Catalyzed Enantioselective Amidation of Ferrocenes Directed by Thioamides under Mild Conditions

Yan-Hua Liu et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chiral Sulfoxide Ligands in Asymmetric Catalysis

Tao Jia et al.

TOPICS IN CURRENT CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting CpXRhIII-Catalyzed C-H Functionalization

Marcus Brauns et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

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

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Chiral 2-Aryl Ferrocene Carboxylic Acids for the Catalytic Asymmetric C(sp3)-H Activation of Thioamides

Daichi Sekine et al.

ORGANOMETALLICS (2019)

添加到收藏夹

Review Chemistry, Physical

Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization

Johannes Diesel et al.

ACS CATALYSIS (2019)

添加到收藏夹

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)

添加到收藏夹

Review Chemistry, Multidisciplinary

Conversion and degradation pathways of sulfoximines

Stefan Wiezorek et al.

CHEMICAL SOCIETY REVIEWS (2019)

添加到收藏夹

Review Multidisciplinary Sciences

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

Tyler G. Saint-Denis et al.

SCIENCE (2018)

添加到收藏夹

Article Chemistry, Organic

Stereospecific C-H activation as a key step for the asymmetric synthesis of various biologically active cyclopropanes

S. Jerhaoui et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantiodivergent Desymmetrization in the Rhodium( III)-Catalyzed Annulation of Sulfoximines with Diazo Compounds

Bingxue Shen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

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)

添加到收藏夹

Article Chemistry, Medicinal

Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery

Marcus Frings et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Physical

Palladium-Catalyzed β-C-H Arylation of Alkyl Carboxamides with Sterically Hindered Aryl Iodides Using ortho-Sulfinyl Aniline Auxiliaries

Delong Mu et al.

ACS CATALYSIS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereoselective Sulfinyl Aniline-Promoted Pd-Catalyzed C-H Arylation and Acetoxylation of Aliphatic Amides

Soufyan Jerhaoui et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

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

Christopher G. Newton et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

Sylwia Otocka et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantiopure Sulfinyl Aniline as a Removable and Recyclable Chiral Auxiliary for Asymmetric C(sp3)-H Bond Activation

Soufyan Jerhaoui et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Organocatalytic Kinetic Resolution of Sulfoximines

Shunxi Dong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Development of Chiral Sulfoxide Ligands for Asymmetric Catalysis

Barry M. Trost et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

The emergence of sulfoxides as efficient ligands in transition metal catalysis

Gellert Sipos et al.

CHEMICAL SOCIETY REVIEWS (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

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

Chao Zheng et al.

RSC ADVANCES (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Sulfoximines: A Neglected Opportunity in Medicinal Chemistry

Ulrich Luecking

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Nitrene Transfer to Sulfides Catalyzed by a Chiral Iron Complex

Jun Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric C(sp2)-H Activation

Joanna Wencel-Delord et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

添加到收藏夹

Review Chemistry, Multidisciplinary

Enantiopure sulfoxides: recent applications in asymmetric synthesis

M. Carmen Carreno et al.

CHEMICAL COMMUNICATIONS (2009)

添加到收藏夹

Review Chemistry, Multidisciplinary

Role of sulfur chirality in the chemical processes of biology

R Bentley

CHEMICAL SOCIETY REVIEWS (2005)

添加到收藏夹

Review Chemistry, Multidisciplinary

Sulfoximines: Synthesis and catalytic applications

H Okamura et al.

CHEMISTRY LETTERS (2004)

添加到收藏夹

Article Chemistry, Multidisciplinary

Iron-catalyzed asymmetric sulfide oxidation with aqueous hydrogen peroxide

J Legros et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.