☆ 4.8 Article

Enantioselective synthesis of α-aminoboronates by NiH-catalysed asymmetric hydroamidation of alkenyl boronates

NATURE COMMUNICATIONS (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

Enantioselective NiH-Catalyzed Reductive Hydrofunctionalization of Alkenes

Yuli He et al.

Summary: Enantioselective NiH-catalyzed reductive hydrofunctionalization of olefins has gained much attention in recent years. By using simple chiral ligands, a variety of functionalized olefins and electrophiles can undergo diverse transformations to yield hydrofunctionalized products with high regio- and enantioselectivity. This review discusses the background, major progress and mechanistic investigations of this reaction.

CHINESE JOURNAL OF CHEMISTRY (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Hydroamination, Aminoboration, and Carboamination with Electrophilic Amination Reagents: Umpolung-Enabled Regio- and Stereoselective Synthesis of N-Containing Molecules from Alkenes and Alkynes

Koji Hirano et al.

Summary: This Perspective describes recent advances in highly selective amination reactions using electrophilic amination reagents. By utilizing the concept of nitrogen umpolung, challenging aminofunctionalizations of alkenes and alkynes have been achieved, leading to densely functionalized complex and often chiral alkylamines with high selectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Organic

Enantioselective Rhodium-Catalyzed Hydrogenation of (Z)-N-Sulfonyl-α-dehydroamido Boronic Esters

Zhenya Li et al.

Summary: Highly enantioselective hydrogenation of (Z)-N-sulfonyl-α-dehydroamido boronic esters using a JosiPhos-type ligand is realized for the first time. This method enables the convenient synthesis of a series of enantio-enriched N-sulfonyl-α-amido boronic esters with good yields and excellent enantioselectivities (up to 99% ee).

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety

Andrej Sterman et al.

Summary: This work describes the preparation and application of primary trifluoroborate-iminiums (pTIMs) as a new and valuable class of organoboron derivatives. Highly enantioselective hydrogenation reactions were used to obtain chiral primary trifluoroborate-ammoniums (pTAMs). A facile conversion method using hexamethyldisiloxane/aqueous HCl was then used to synthesize diverse chiral alpha-aminoboronic acids from chiral pTAMs. The synthesis of optically pure anti-cancer drugs bortezomib and ixazomib demonstrated the practicality of this method.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Endo-Selective Intramolecular Alkyne Hydroamidation Enabled by NiH Catalysis Incorporating Alkenylnickel Isomerization

Hoonchul Choi et al.

Summary: Intramolecular alkyne hydroamidation is a direct method for the synthesis of valuable cyclic enamides. This study reports a new catalyst that achieves high internal selectivity and has a broad reaction scope. Mechanistic investigations reveal key steps in the reaction and uncover previously unknown details. This method has potential for practical synthetic applications.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Streamlined Alkylation via Nickel-Hydride-Catalyzed Hydrocarbonation of Alkenes

Zhikun Zhang et al.

Summary: This article summarizes the importance of compounds rich in sp(3)-hybridized carbons in drug discovery, and introduces the nickel-catalyzed hydrocarbonation of alkenes as a potentially efficient method to synthesize these compounds. The article focuses on enantioselective reactions and provides a critical discussion of the state and challenges of the field.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

NiH-catalyzed asymmetric hydroalkynylation of α,fl-unsaturated amides

Yuanzheng Cheng et al.

Summary: An enantioselective NiH-catalyzed hydroalkynylation of α,β-unsaturated amides is described, which can proceed under mild conditions and is applicable to a wide range of substrates.

GREEN SYNTHESIS AND CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides

Sergio Cuesta-Galisteo et al.

Summary: This study presents a nickel-catalyzed asymmetric reductive hydroarylation method for synthesizing enantioenriched alpha-arylbenzamides. By using a BIm ligand, diethoxymethylsilane, and aryl halides, aryl groups can be selectively introduced to the internal position of the olefin, creating a new stereogenic center alpha to the N atom with neutral reagents and mild reaction conditions. This provides a straightforward route to pharmacologically relevant motifs found in anticancer drugs, SARS-CoV PLpro inhibitors, and KCNQ channel openers.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ligand-Enabled NiH-Catalyzed Migratory Hydroamination: Chain Walking as a Strategy for Regiodivergent/Regioconvergent Remote sp3C-H Amination

Yulong Zhang et al.

Summary: This study presents a non-directed, remote sp(3)C-H amination process with predictable and switchable regioselectivity, demonstrating efficient functionalization reactions. Depending on the choice of ligand, different types of functionalization products can be obtained, expanding the possibilities of introducing functional groups.

CCS CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

Jiandong Liu et al.

Summary: A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, yielding benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction prevent olefinic products from further isomerization or subsequent alkenylation, and catalytic enantioselective hydroalkenylation of styrenes was achieved using a chiral bisoxazoline ligand.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Deyun Qian et al.

Summary: A nickel-catalyzed hydroalkylation method has been developed to assemble a wide range of chiral alkyl amines with high regio- and enantioselectivity from enecarbamates and alkyl halides. The method is suitable for both nonactivated and activated alkyl halides, producing enantiomerically enriched amines with high functional group tolerance.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective C(sp3)-C(sp3) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis

Srikrishna Bera et al.

Summary: The enantioselective cross-coupling of non-activated alkyl halides with alkenyl boronates enables the synthesis of chiral alkyl boronates, which is a useful method for drug development. This reaction proceeds via nickel hydride insertion into an internal alkene followed by nickel-catalysed alkyl-alkyl cross-coupling.

NATURE CHEMISTRY (2021)

添加到收藏夹

Article Multidisciplinary Sciences

NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines

Yuli He et al.

Summary: The authors report an enantio- and regio-selective reductive hydroarylation of N-acyl enamines with a NiH/chiral bis-imidazoline catalytic system affording a range of enantioenriched benzylamines.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines

Jia-Wang Wang et al.

Summary: In order to increase the reliability and success rate of drug discovery, researchers have developed a new method to synthesize drug-like alpha-branched chiral amines and derivatives by nickel-catalyzed asymmetric reductive hydroalkylation of enamides and enecarbamates.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates

Yao Zhang et al.

Summary: By synergistically combining a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioen-riched alpha-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp(3))-H arylation process.

CHEM (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Merging NiH Catalysis and Inner-Sphere Metal-Nitrenoid Transfer for Hydroamidation of Alkynes

Xiang Lyu et al.

Summary: A NiH-catalyzed strategy for the hydroamidation of alkynes with dioxazolones has been reported in this study, providing synthetically useful secondary enamides in (E)-anti-Markovnikov or Markovnikov selectivity. The reaction is viable for various alkynes and functional groups, with H2O found to be essential for high catalyst turnovers. Inner-sphere nitrenoid transfer is proposed as a key component in outcompeting undesired processes in the Ni catalysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations

Shan Wang et al.

Summary: Chiral aliphatic amine and alcohol derivatives are difficult to access due to the challenge to differentiate between spatially and electronically similar alkyl groups. By utilizing a nickel-catalyzed enantioselective hydroalkylation, enantioenriched alpha-branched aliphatic acyl amines and esters can be efficiently synthesized with good yields and excellent enantioselectivity.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Facile Synthesis of Chiral Arylamines, Alkylamines and Amides by Enantioselective NiH-Catalyzed Hydroamination

Lingpu Meng et al.

Summary: Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed using NiH catalysis with a simple bioxazoline ligand under mild conditions. A variety of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by employing nitroarenes, hydroxylamines and dioxazolones as amination reagents. Chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones

Bingnan Du et al.

Summary: A NiH-catalyzed thioether-directed cyclometalation strategy allows for remote methylene C-H bond amidation of unactivated alkenes. This strategy shows high yields and remarkable regioselectivity in the preparation of amide products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Nickel-catalysed migratory hydroalkynylation and enantioselective hydroalkynylation of olefins with bromoalkynes

Xiaoli Jiang et al.

Summary: The study presents a new synthetic method for the high-yielding and regioselective synthesis of enantioenriched benzylic alkynes. These compounds serve as important synthetic intermediates with a wide range of potential applications.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

alpha-Aminoboronates: recent advances in their preparation and synthetic applications

Wenbo Ming et al.

Summary: Alpha-aminoboronic acids and their derivatives are widely used as bioactive agents, with several compounds approved by the FDA as protease inhibitors. In organic synthesis, they are important reagents for the synthesis of chiral molecules and valuable organic compounds.

CHEMICAL SOCIETY REVIEWS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Olefins with α-Heteroatom Phosphorus or Sulfur Alkyl Electrophiles

Shi-Jiang He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes

Xuzhong Shen et al.

NATURE COMMUNICATIONS (2020)

添加到收藏夹

Article Chemistry, Physical

Asymmetric Hydrogenation of α-Boryl Enamides Enabled by Nonbonding Interactions

Dongyang Fan et al.

ACS CATALYSIS (2020)

添加到收藏夹

Article Chemistry, Physical

Cascade CuH-catalysed conversion of alkynes into enantioenriched 1,1-disubstituted products

De-Wei Gao et al.

NATURE CATALYSIS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition

Richard Y. Liu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer

Casey B. Roos et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chemoselective Cross-Coupling of gem-Borazirconocene Alkanes with Aryl Halides

Chao Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent advances in nickel-catalyzed reductive hydroalkylation and hydroarylation of electronically unbiased alkenes

Xiao-Xu Wang et al.

SCIENCE CHINA-CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes

Jinwon Jeon et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Catalytic asymmetric addition of an amine N-H bond across internal alkenes

Yumeng Xi et al.

NATURE (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters

Yazhou Lou et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols

Yulong Zhang et al.

NATURE COMMUNICATIONS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ni-Catalyzed Enantioselective Intermolecular Hydroamination of Branched 1,3-Dienes Using Primary Aliphatic Amines

Gael Tran et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Site-Selective Catalytic Deaminative Alkylation of Unactivated Olefins

Shang-Zheng Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Non-C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)-H Amidation

Zijun Zhou et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Regiodivergent and Enantioselective Hydroboration of Enamides

Xiao-Yan Bai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

NiH-Catalyzed Remote Asymmetric Hydroalkylation of Alkenes with Racemic -Bromo Amides

Fang Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp(3))-H Alkylation of Alkenes

Fang Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

CuH-Catalyzed Asymmetric Hydroamidation of Vinylarenes

Yujing Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Selective formation of gamma-lactams via C-H amidation enabled by tailored iridium catalysts

Seung Youn Hong et al.

SCIENCE (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Remote sp(3) C-H Amination of Alkenes with Nitroarenes

Jichao Xiao et al.

CHEM (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent Advances in Hydrometallation of Alkenes and Alkynes via the First Row Transition Metal Catalysis

Jianhui Chen et al.

CHINESE JOURNAL OF CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of alpha-Amidoboronates Catalyzed by Planar-Chiral NHC-Cu(I) Complexes

C. Benjamin Schwamb et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation

Sophia L. Shevick et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Highly Enantiospecific Borylation for Chiral α-Amino Tertiary Boronic Esters

Qingqing Qi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Catalytic enantioconvergent coupling of secondary and tertiary electrophiles with olefins

Zhaobin Wang et al.

NATURE (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mild and Regioselective Benzylic C-H Functionalization: Ni-Catalyzed Reductive Arylation of Remote and Proximal Olefins

Yuli He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water

Morgane Gaydou et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

The versatility of boron in biological target engagement

Diego B. Diaz et al.

NATURE CHEMISTRY (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Synthesis of alpha-aminoboronic acids

Patricia Andres et al.

CHEMICAL SOCIETY REVIEWS (2016)

添加到收藏夹

Article Multidisciplinary Sciences

Practical carbon-carbon bond formation from olefins through nickel-catalyzed reductive olefin hydrocarbonation

Xi Lu et al.

NATURE COMMUNICATIONS (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Amidation of Unactivated C(sp3)H Bonds

He Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Late Transition Metal-Catalyzed Hydroamination and Hydroamidation

Liangbin Huang et al.

CHEMICAL REVIEWS (2015)

添加到收藏夹

Article Chemistry, Medicinal

Discovery of a Cyclic Boronic Acid β-Lactamase Inhibitor (RPX7009) with Utility vs Class A Serine Carbapenemases

Scott J. Hecker et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides

Naifu Hu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric Synthesis of α-Aminoboronic Acid Derivatives by Copper-Catalyzed Enantioselective Hydroamination

Daiki Nishikawa et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C-H Amination with a New Type of Amidating Reagent

Yoonsu Park et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes

Shaolin Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-Catalyzed Intermolecular Regioselective Hydroamination of Styrenes with Polymethylhydrosiloxane and Hydroxylamines

Yuya Miki et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates

Kai Hong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantio- and Regioselective CuH-Catalyzed Hydroamination of Alkenes

Shaolin Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric synthesis of alpha-amino boronate esters via organocatalytic pinacolboryl addition to tosylaldimines

Cristina Sole et al.

CHEMICAL COMMUNICATIONS (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Inversion or Retention? Effects of Acidic Additives on the Stereochemical Course in Enantiospecific Suzuki-Miyaura Coupling of α-(Acetylamino)benzylboronic Esters

Tomotsugu Awano et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric Intermolecular Hydroamination of Unactivated Alkenes with Simple Amines

Alexander L. Reznichenko et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines

Melissa A. Beenen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.